Benzyl Bromide → HCID 59508044、化合物

HRID 1958649ノート

反応式

HRID 1958649 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.[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(OCC)(=O)C>ClCCl.O>[CH2:33]([N:21]1[CH2:22][CH2:23][CH:18]([C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:19][CH2:20]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 59508043HCID 59508043、化合物

生成物 1

HCID 59508044HCID 59508044、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 2-(2-methoxy-pyridin-3-yl)-3-piperidin-4-yl-1H-indole (0.13 g, 0.42 mmol) in dichloromethane (5 ml) was added diisopropylethylamine (0.22 ml, 1.25 mmol) followed by the benzyl bromide (0.075 g, 0.44 mmol). The reaction was stirred at room temperature for 2 h followed by addition of ethyl acetate and water. The organic layer was separated and washed with water, dried using Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography (SiO2, 100% EtOAc). The desired product was obtained as a yellow solid (0.080 g, 48%). M.p.=97-101° C.; 400 M Hz 1H NMR (DMSO-d6) 10.99 (s, 1H), 8.24 (dd, J1=7.2 Hz, J2=2.0 Hz, 1H), 7.70 (m, 2H), 7.34-7.24 (m, 6H), 7.13 (dd, J1=7.6 Hz, J2=5.2 Hz, 1H), 7.07 (m, 1H0, 6.98 (m, 1H), 3.86 (s, 3H), 3.48 (s, 2H), 2.92 (m, 2H), 2.56 (m, 1H), 2.15 (m, 2H), 1.93 (m, 2H), 1.64 (m, 2H); LCMS: 398.76 (M+1).

後処理

  1. customThe organic layer was separated
  2. washwashed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography (SiO2, 100% EtOAc)

出典と根拠

ORDレコード
ord-5ebd402406484d9b8f1b48e35ada00d3
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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