ChemicalBook CAS DataBase List tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate

tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate synthesis

6synthesis methods

Product Name:tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate
CAS Number:365996-06-1
Molecular formula:C11H15BrN2O2S
Molecular Weight:319.22

TERT-BUTYL 2-AMINO-6,7-DIHYDROTHIAZOLO[5,4-C]PYRIDINE-5(4H)-CARBOXYLATE

365996-05-0

365996-06-1

Method G - Step e: Synthesis of tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate [0134] To a 100 mL DMF solution containing isoamyl nitrite (8.8 mL, 62.8 mmol) and copper(II) bromide (10.7 g, 48 mmol) was added tert-butyl 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (10 g, 39.2 mmol) at 0°C. The reaction was carried out at 40°C and the reaction mixture was purified. The reaction mixture was stirred at 40°C for 30 min and then concentrated by evaporation. The concentrate was dissolved in 50 mL of water and extracted with dichloromethane (100 mL × 2). The organic phases were combined, washed with brine (30 mL × 2), and dried over anhydrous sodium sulfate. Purification by silica gel column chromatography (eluent: dichloromethane) afforded the target product tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (5.3 g, 42.4%) as a yellow solid.

540-80-7
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$29.00/25 g

365996-05-0
164 suppliers
$54.00/1 / G

365996-06-1
155 suppliers
$56.00/250mg

Yield: 44%

Reaction Conditions:

with copper(ll) bromide in dichloromethane at 0; for 3 h;

Steps:

29.3 tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate
To a stuffing solution of tert-butyl 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine- 5(4H)-carboxylate (2.0 g, 7.84 mmol) in DCM (30 mL) was added tert-butyl nitrite (1.24 g, 12 mmol) and CuBr2 (1.78 g, 8 mmol). The solution was stirred at 0 °C for 3h. Once LCMS showed the reaction to be complete, solvents were then evaporated and the residue was purified with column separation to afford desired product as white solid (1.1 g, yield: 44%);LCMS: 318.9/320.9 (M+1).

References:

EPIZYME, INC.;DUNCAN, Kenneth, W.;CHESWORTH, Richard;MUNCHHOF, Michael, John;SHAPIRO, Gideon WO2015/200677, 2015, A2 Location in patent:Paragraph 00647; 00648

365996-05-0
164 suppliers
$54.00/1 / G

365996-06-1
155 suppliers
$56.00/250mg

References

7789-45-9 Synthesis