Ethanesulfonyl chloride → HCID 178477688、化合物

HRID 1888212ノート

反応式

HRID 1888212 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]#[N:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(C(C)C)CC)(C)C.[CH2:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]#[N:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:13]1[CH2:18][CH2:17][N:16]([S:30]([CH2:28][CH3:29])(=[O:32])=[O:31])[CH2:15][CH2:14]1

参加物

5

反応物 3

HCID 11667Ethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178509434HCID 178509434、化合物2 回

生成物 1

HCID 178477688HCID 178477688、化合物収率 42.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The crude 5-bromo-3-(4-piperidinyl)-1H-indazole-7-carbonitrile (Intermediate 9) (0.222 g, 0.493 mmol) was suspended in dichloromethane (5 mL) and treated with diisopropylethyl amine (0.257 mL, 1.48 mmols), and ethane sulfonyl chloride (0.070 mL, 0.74 mmols) at ambient temperature. After 2 hrs, the mixture was concentrated to dryness in vacuo at ambient temperature, treated with water (25 mL), and extracted with dichloromethane (100 mL). The organic phase was washed with water, dried over MgSO4, filtered, and concentrated to give a light brown solid. This was purified by combiflash (column 10 g, eluting with 100% dichloromethane, 5% ethyl acetate/dichloromethane, 30% ethyl acetate/dichloromethane) to give the title compound (0.083 g, 24%).

後処理

  1. concentrationthe mixture was concentrated to dryness in vacuo at ambient temperature
  2. additiontreated with water (25 mL)
  3. extractionextracted with dichloromethane (100 mL)
  4. washThe organic phase was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a light brown solid
  9. customThis was purified by combiflash (column 10 g, eluting with 100% dichloromethane, 5% ethyl acetate/dichloromethane, 30% ethyl acetate/dichloromethane)

出典と根拠

ORDレコード
ord-eed87d0bc9cc4cb482088d501f566213
出典データセット
uspto-grants-2013_08
特許番号
US08501780B2

反応ノート

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