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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

HRID 902533
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인쇄 미리보기

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HRID 902533 반응식
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]
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참가 물질

4

반응물 2

HCID 65578Oxalyl chlorideHCID 597020997-(3-Fluoro-benzyl)-4-hydroxy-2-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

생성물 1

HCID 597020794-Chloro-7-(3-fluoro-benzyl)-2-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
75 °C

실험 절차

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).

후처리

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by cold water
  5. customdried

출처 및 근거

ORD 기록
ord-c784f341a6424e1cb3689eab3c98a3d6
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07365200B2

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