3-Chlorobenzenesulphonyl chloride → Ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridine-5-carboxylate

HRID 573592노트

반응식

HRID 573592 반응식
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:17])=[CH:16][C:3]=12.CC(C)([O-])C.[Na+].[Cl:24][C:25]1[CH:26]=[C:27]([S:31](Cl)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1>C1COCC1.CN(C=O)C.O>[Br:17][C:15]1[S:14][C:4]2=[N:5][C:6]([CH3:13])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2]([NH:1][S:31]([C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([Cl:24])[CH:26]=3)(=[O:33])=[O:32])=[C:3]2[CH:16]=1

참가 물질

7

반응물 3

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 23676156Sodium t-butoxideHCID 68323734Ethyl 4-amino-2-bromo-6-methylthieno[2,3-b]pyridine-5-carboxylate

생성물 1

HCID 68323811Ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridine-5-carboxylate수율 69.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

Alternatively, to a stirred solution of ethyl 4-amino-2-bromo-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 66) (3.76 g, 11.93 mmol) in THF (60 mL) and DMF (30 mL) was added sodium tert-butoxide (2.87 g, 29.8 mmol) and 3-chlorobenzenesulfonyl chloride (3.36 mL, 23.86 mmol). The reaction mixture was stirred at RT under nitrogen for ca. 30 min and was then diluted with water (ca. 30 mL) and concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a gradient of 0-50% ethyl acetate/DCM, to afford the title compound (4.06 g). Alternatively, to a stirred solution of ethyl 4-amino-2-bromo-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 66) (7 g, 22.21 mmol) in THF (100 mL) and DMF (50 mL) was added sodium tert-butoxide (5.34 g, 55.5 mmol) and 3-chlorobenzenesulfonyl chloride (6.25 mL, 44.4 mmol). The reaction mixture was then stirred at RT under nitrogen for ca. 30 min. The reaction mixture was quenched with saturated NH4Cl solution (ca. 200 mL) and extracted with DCM (ca. 80 mL×5). The combined organics were dried and concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a gradient of 0-50% ethyl acetate in DCM, to afford material (8.24 g). 200 mg of the material was re-purified with a gradient of 0-30% ethyl acetate in DCM, to afford the title compound (115 mg).

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by chromatography on silica
  3. washeluting with a gradient of 0-50% ethyl acetate/DCM

출처 및 근거

ORD 기록
ord-0d3f860b90d34afb8b292e4c782b42c0
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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