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

HRID 573587ノート

反応式

HRID 573587 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-691da8ae38074738b385c97d2d20bfdf
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

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