Boron tribromide → 2-(6-Hydroxy-2-naphthyl)-3-pentyl-1H-indole

HRID 495498노트

반응식

HRID 495498 반응식
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[NH:14][C:15]3[C:20]([C:21]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:7]=[CH:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[NH:14][C:15]3[C:20]([C:21]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:7]=[CH:6]2

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 223273422-(6-methoxy-2-naphthyl)-3-pentyl-1H-indole

생성물 1

HCID 223273352-(6-Hydroxy-2-naphthyl)-3-pentyl-1H-indole수율 77.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2-(6-methoxy-2-naphthyl)-3-pentyl-1H-indole (0.915 g, 2.66 mmol) in CH2Cl2 (30 mL) cooled to −78° C. was added BBr3 (9.86 mL, 1.0 M in CH2Cl2, 9.86 mmol) dropwise. The reaction was stirred at this temperature for 0.5 h and then warmed to rt for 2 h. The reaction mixture was quenched with MeOH (˜5 mL) followed by dilution with H2O (20 mL) and EtOAc (200 mL). The organic layer was washed with brine (20 mL) and then dried (Na2SO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 20% EtOAc:petroleum ether gradient) to afford the product (0.677 g, 77%) as a foamy solid; 1H NMR (DMSO-d6) δ 0.83 (t, J=7.3 Hz, 3H), 1.23-1.42 (m, 4H), 1.58-1.76 (m, 2H), 2.89 (t, J=8.2 Hz, 2H), 7.00 (t, J=8.2 Hz, 1H), 7.06-7.19 (m, 3H), 7.35 (d, J=8.2 Hz, 1H), 7.53 (d, J=8.2, 1H), 7.67 (d, J=9.1 Hz, 1H), 7.74-7.88 (m, 2H), 7.98 (s, 1H), 9.83 (s, 1H), 11.14 (s, 1H); mass spectrum [(+) ESI], m/z 330 (M+H)+ and [(−) ESI], m/z 328 (M−H)−.

후처리

  1. customThe reaction mixture was quenched with MeOH (˜5 mL)
  2. washThe organic layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationAfter concentration
  5. customthe residue was purified by the Biotage Flash 40 apparatus (10 to 20% EtOAc:petroleum ether gradient)

출처 및 근거

ORD 기록
ord-347b7ab12e3c406298183ede6583e943
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939886B2

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