Oxalyl chloride → 4-Chloro-7-(3-fluoro-benzyl)-2-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester
Reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH2:7]([O:9][C:10]([C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[C:15]2[S:27][C:28]([CH3:30])=[CH:29][C:14]=2[C:13]=1O)=[O:11])[CH3:8]>CN(C=O)C>[CH2:7]([O:9][C:10]([C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[C:15]2[S:27][C:28]([CH3:30])=[CH:29][C:14]=2[C:13]=1[Cl:4])=[O:11])[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Oxalyl chloride (4.83 mL, 0.055 mol) was added to a solution of 7-(3-fluoro-benzyl)-4-hydroxy-2-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester (69) (8 g, 0.022 mol) in DMF at −30° C. under argon. The temperature was raised gradually to 75° C. and stirred for 3 h. The solution was cooled and poured into ice water. The solids formed were filtered, washed by cold water and dried to yield 6.8 g (82%) of 4-chloro-7-(3-fluoro-benzyl)-2-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester. 1H-NMR (DMSO-d6) δ 1.30 (t, J=7.2 Hz, 3H), 2.45 (d, J=1.2 Hz, 3H), 4.33 (q, J=7.2 Hz, 2H), 5.31 (s, 2H), 7.05 (d, J=1.2 Hz, 1H), 7.09-7.17 (m, 3H), 7.40 (m, 1H) ppm, EIMS m/z 380 (M+1).
Workup
- temperatureThe solution was cooled
- customThe solids formed
- filtrationwere filtered
- washwashed by cold water
- customdried
Sources & evidence
- ORD record
- ord-c784f341a6424e1cb3689eab3c98a3d6
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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