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

HRID 573582노트

반응식

HRID 573582 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:18])=[C:16]([CH3:17])[C:3]=12.CC(C)([O-])C.[Na+].[Cl:25][C:26]1[CH:27]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>CN(C=O)C.C(OCC)(=O)C.O>[Br:18][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:32]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([Cl:25])[CH:27]=3)(=[O:34])=[O:33])=[C:3]2[C:16]=1[CH3:17]

참가 물질

7

반응물 3

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 23676156Sodium t-butoxideHCID 68324019Ethyl 4-amino-2-bromo-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate

생성물 1

HCID 68324133Ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate수율 45.7%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of ethyl 4-amino-2-bromo-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate (Description 31) (500 mg, 1.519 mmol) in DMF (10 mL) was added sodium tert-butoxide (365 mg, 3.80 mmol) and 3-chlorobenzenesulfonyl chloride (0.428 mL, 3.04 mmol). The whole mixture was stirred at RT under nitrogen for ca. 1.5 h. The reaction mixture was then diluted with ethyl acetate (ca. 30 mL) and water (ca. 50 mL). The organic phase was separated and the aqueous phase re-extracted with ethyl acetate (ca. 30 mL×2). The combined organic phase was dried over Na2SO4 and the solvent concentrated in vacuo. The residue was purified by normal phase chromatography, eluting with a gradient of 0-50% ethyl acetate in cyclohexane, to give the title compound (350 mg). LCMS (A) m/z: 504/506 [M+1]+, Rt 1.59 min (acidic).

후처리

  1. customThe organic phase was separated
  2. extractionthe aqueous phase re-extracted with ethyl acetate (ca. 30 mL×2)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationthe solvent concentrated in vacuo
  5. customThe residue was purified by normal phase chromatography
  6. washeluting with a gradient of 0-50% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-41e56b671d0d4c54a8c3b9597e3f09d1
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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