5-Bromo-2-methoxybenzene-1-sulfonyl chloride → HCID 57473902、化合物

HRID 1868408ノート

反応式

HRID 1868408 の反応式
[F:1][C:2]([F:16])([F:15])[CH:3]([NH2:14])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[Br:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([S:24](Cl)(=[O:26])=[O:25])[CH:23]=1>N1C=CC=CC=1.C(O)(=O)C.C(OCC)(=O)C>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([S:24]([NH:14][CH:3]([CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)[C:2]([F:1])([F:15])[F:16])(=[O:25])=[O:26])[CH:23]=1

参加物

6

反応物 2

HCID 5200205-Bromo-2-methoxybenzene-1-sulfonyl chlorideHCID 539884361,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-amine

生成物 1

HCID 57473902HCID 57473902、化合物収率 32%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

A mixture of 100 mg (0.44 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 143 mg (0.50 mmol) of 5-bromo-2-methoxybenzenesulfonyl chloride in 4 mL of pyridine was warmed at 65° C. After 16 hours, the mixture was cooled and concentrated to afford a thick oily residue. The residue was diluted with 10% acetic acid and extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, decanted, and concentrated in vacuo. The crude material was purified by preparative TLC using ethyl acetate-hexanes (15:85). Material from the plate was isolated by suspending the silica gel in ethyl acetate followed by filtration. The filtrate was concentrated in vacuo to afford 66 mg (32%) of the title compound as a crystalline solid.

後処理

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated
  3. customto afford a thick oily residue
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. customdecanted
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by preparative TLC
  10. customMaterial from the plate was isolated
  11. filtrationfollowed by filtration
  12. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-011b92e0a15f42ecb0ea97c682b9fc53
出典データセット
uspto-grants-2009_12
特許番号
US07635711B2

反応ノート

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