Water → Ethyl 5-(4-chlorobenzoyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate

HRID 468682Notes

Reaction equation

HRID 468682 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1.F[P-](F)(F)(F)(F)F.FC(N(C)C)=[N+](C)C.O>CN(C)C=O.C(N(CC)C(C)C)(C)C>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:6]2[CH2:7][CH2:8][C:9]3[S:1][C:2]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][C:4]=3[CH2:5]2)=[O:21])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 63184-Chlorobenzoic AcidHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 45480492Ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate

Product 1

HCID 58157572Ethyl 5-(4-chlorobenzoyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylateYield 53.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate (0.237 g, 1.12 mmol), 4-chlorobenzoic acid (0.228 g, 1.46 mmol) in N,N-dimethylformamide (6 mL) was added a solution of fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (0.444 g, 1.68 mmol) in N,N-diisopropylethylamine (0.6 mL). The reaction solution was then stirred overnight at room temperature. Water was then added and the mixture was extracted into ethyl acetate. The organic layer was washed with brine and evaporated. Purification of the residue obtained on silica gel (0-10% ethyl acetate/DCM) afforded a sticky white solid (208 mg, 53%). LCMS (FA) ES+ 350.

Workup

  1. extractionthe mixture was extracted into ethyl acetate
  2. washThe organic layer was washed with brine
  3. customevaporated
  4. customPurification of the residue
  5. customobtained on silica gel (0-10% ethyl acetate/DCM)

Sources & evidence

ORD record
ord-edaca93c41d047179e29e65cf594932e
Source dataset
uspto-grants-2014_01
Patent number
US08624040B2

Reaction notes

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