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 2282185Notes

Reaction equation

HRID 2282185 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][C:13]1[C:21]([C:22]2[S:23]C(C3NC=NN=3)=C(C3C=CC=CC=3)[N:26]=2)=[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]2[N:14]=1.Cl[CH:39]([C:45]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[F:53])=O)[C:40]([O:42][CH2:43][CH3:44])=[O:41]>CC(O)C>[F:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[C:45]1[N:26]=[C:22]([C:21]2[C:13]([CH3:12])=[N:14][N:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=23)[S:23][C:39]=1[C:40]([O:42][CH2:43][CH3:44])=[O:41]

Participants

4

Reactant 2

HCID 18473854Ethyl 2-chloro-2-(2-fluorobenzoyl)acetateHCID 178427648HCID 178427648, compound

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-B (v), ethyl 2-chloro-3-(2-fluorophenyl)-3-oxopropanoate (1.0 g, 4.09 mmol) produced 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-f1aba4b8fe9f4cb382f9d8d869342cbc
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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