Benzyl Bromide → Methyl 4-(benzyloxy)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate

HRID 2282197Notes

Reaction equation

HRID 2282197 reaction equation
[OH:1][C:2]1[N:3]=[C:4]([C:11]2[C:12]([CH3:20])=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=23)[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[CH2:27]([O:1][C:2]1[N:3]=[C:4]([C:11]2[C:12]([CH3:20])=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=23)[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 136376955Methyl 4-hydroxy-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 66855450Methyl 4-(benzyloxy)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using methyl 4-hydroxy-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate (800 mg, 2.5 mmol) produced in Example 13-B(i), potassium carbonate (1.9 g, 5.9 mmol), benzyl bromide (2.8 g, 12 mmol) and N,N-dimethylformamide (50 mL) as starting materials and in the same manner as in Example 27-B(i), the title compound (560 mg, 60%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-c9688d7c95d840dea42d0b2571ac85b7
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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