Benzyl Bromide → HCID 59508044, 화합물

HRID 1958649노트

반응식

HRID 1958649 반응식
[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

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 59508043HCID 59508043, 화합물

생성물 1

HCID 59508044HCID 59508044, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5ebd402406484d9b8f1b48e35ada00d3
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410144B2

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