Triethylsilane → 3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol

HRID 1766231

반응식

HRID 1766231 반응식
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.C([SiH](CC)CC)C>ClCCl>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 149732073-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indol-5-ol

생성물 1

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-ol수율 90.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

By a method similar to Preparation 20, using 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-hydroxy-1H-indole (1.25 g, 5.47 mmol) in dichloromethane (5 mL) trifluoroacetic acid (5 mL), triethylsilane (875 mL, 6.0 mmol) afforded 1.14 g (90%) of the title compound as a tan solid: mp=233-237° C.; 1H NMR (400 MHz, dmso-d6): 10.41 (br s, 1H), 8.52 (br s, 1H), 7.08 (d, 1H, J=8.0 Hz), 6.92 (d, 1H, J=2.0 Hz), 6.80 (d, 1H, J=2.0 Hz), 6.53 (dd, 1H, J=8.4, 2.0 Hz), 2.84 (br d, 2H, J=11.2 Hz), 2.63-2.50 (m, 1H), 2.19 (s, 3H), 2.08-1.97 (m, 2H), 1.85 (br d, 2H, J=12.0 Hz), 1.72-1.57 (m 2H); MS (ES+) m/e 231.0 (M+1).

후처리

  1. customBy a method similar to Preparation 20

출처 및 근거

ORD 기록
ord-93299e3949c547b185d8bd2dc02fde9c
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230011B2

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