Ethyl 2-chloro-2-(2-fluorobenzoyl)acetate → Ethyl 4-(2-fluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate

HRID 1530023Notes

Reaction equation

HRID 1530023 reaction equation
Cl.[CH3:2][C:3]1[C:11]([C:12](=[S:14])[NH2:13])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.Cl[CH:16]([C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30])=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CC(O)C>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:22]1[N:13]=[C:12]([C:11]2[C:3]([CH3:2])=[N:4][N:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=23)[S:14][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 2

HCID 18473854Ethyl 2-chloro-2-(2-fluorobenzoyl)acetateHCID 866495852-Methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride

Product 1

HCID 66855412Ethyl 4-(2-fluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylateYield 68.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Using 2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (300 mg, 1.3 mmol) produced in Example 11(v), ethyl 2-chloro-3-(2-fluorophenyl)-3-oxopropanoate (1.0 g, 4.09 mmol) produced in the above and 2-propanol (25 mL) as starting materials and in the same manner as in Example 11(vi), the title compound (341 mg, 68%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-c9added6c89343fb953468b487b04362
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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