Benzenesulfonyl chloride → HCID 59508100、化合物

HRID 1958650ノート

反応式

HRID 1958650 の反応式
[CH3:1][O:2][C:3]1[C:8]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(C(C)C)CC)(C)C.[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:33]1([S:39]([N:21]2[CH2:22][CH2:23][CH:18]([C:17]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:10][C:9]=3[C:8]3[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=3)[CH2:19][CH2:20]2)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

参加物

5

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59508043HCID 59508043、化合物

生成物 1

HCID 59508100HCID 59508100、化合物収率 24.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(2-methoxy-pyridin-3-yl)-3-piperidin-4-yl-1H-indole (0.12 g, 0.39 mmol) in dichloromethane (10 ml) and diisopropylethylamine (0.20 ml, 1.17 mmol) was added phenylsulfonyl chloride (52 μl, 0.41 mmol). The reaction was stirred at room temperature for 4 h and quenched by adding water. The organic layer was separated, washed with aqueous sodium hydroxide, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by a flash chromatography (SiO2, 30% EtOAc in hexane) to give the desired product as a white solid (0.042 g, 24%); M.p.=231-234° C.; 400 MHz 1H NMR (DMSO-d6) δ: 11.00 (s, 1H), 8.20 (dd, J1=0.8 Hz, J2=4.8 Hz, 1H), 7.77 (m, 3H), 7.66 (m, 3H), 7.29 (m, 2H), 7.07 (m, 2H), 6.92 (m, 1H), 3.84 (m, 5H), 2.56 (m, 1H), 2.42 (m, 2H), 2.00 (m, 2H), 1.66 (m, 2H); LCMS: 448.69 [M+H].

後処理

  1. customquenched
  2. additionby adding water
  3. customThe organic layer was separated
  4. washwashed with aqueous sodium hydroxide, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by a flash chromatography (SiO2, 30% EtOAc in hexane)

出典と根拠

ORDレコード
ord-581dca729dd74d889285362bdb05744e
出典データセット
uspto-grants-2013_04
特許番号
US08410144B2

反応ノート

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