Benzenesulfonyl chloride → Ethyl 2-bromo-6-methyl-4-[(phenylsulfonyl)amino]thieno[2,3-b]pyridine-5-carboxylate

HRID 573587노트

반응식

HRID 573587 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+].[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.CN(C=O)C>[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:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:32])=[O:31])=[C:3]2[CH:16]=1

참가 물질

6

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 23676156Sodium t-butoxideHCID 68323734Ethyl 4-amino-2-bromo-6-methylthieno[2,3-b]pyridine-5-carboxylate

생성물 1

HCID 68324051Ethyl 2-bromo-6-methyl-4-[(phenylsulfonyl)amino]thieno[2,3-b]pyridine-5-carboxylate수율 74.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirring mixture of ethyl 4-amino-2-bromo-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 66) (5.84 g, 18.53 mmol) in THF (110 mL) and DMF (55 mL) was added sodium tert-butoxide (4.45 g, 46.3 mmol) and benzenesulfonyl chloride (4.75 mL, 37.1 mmol). The resulting mixture was stirred at RT for 30 min. The reaction mixture was quenched with saturated ammonium chloride solution (ca. 150 mL) and extracted with DCM (80 mL×3). The combined organic layers were dried and concentrated. The residue was purified via normal phase chromatography, eluting with 0-30% ethyl acetate in DCM, to give the title compound (6.27 g). LCMS (A) m/z: 455/457 [M+1]+, Rt 1.35 min (acidic).

후처리

  1. customThe reaction mixture was quenched with saturated ammonium chloride solution (ca. 150 mL)
  2. extractionextracted with DCM (80 mL×3)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe residue was purified via normal phase chromatography
  6. washeluting with 0-30% ethyl acetate in DCM

출처 및 근거

ORD 기록
ord-691da8ae38074738b385c97d2d20bfdf
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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