Water → 1-[4-(2-(Azepan-1-yl)ethoxy)benzyl]-5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole

HRID 1662952노트

반응식

HRID 1662952 반응식
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:22][CH:21]=1)=[C:14]2[CH3:34])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:35]1([CH2:42][CH2:43][O:44][C:45]2[CH:52]=[CH:51][C:48]([CH2:49]Cl)=[CH:47][CH:46]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.O>CN(C=O)C>[N:35]1([CH2:42][CH2:43][O:44][C:45]2[CH:52]=[CH:51][C:48]([CH2:49][N:16]3[C:17]4[C:13](=[CH:12][C:11]([O:10][CH2:3][C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=5)=[CH:19][CH:18]=4)[C:14]([CH3:34])=[C:15]3[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:22][CH:21]=3)=[CH:47][CH:46]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 38247451H-Indole, 3-methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-HCID 98829101-(2-(4-(Chloromethyl)phenoxy)ethyl)azepane

생성물 1

HCID 98958311-[4-(2-(Azepan-1-yl)ethoxy)benzyl]-5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

In an inert atmosphere NaH (2.7 g; 112 mmol) was suspended in DMF (80 ml). At 0-5° C. 5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1H-indole (11 g; 26 mmol) was added and the suspension was stirred for 30 minutes. Then a solution of 4-(2-azepan-1-yl-ethoxy)benzyl chloride (8 g; 26 mmol) in DMF (30 ml) was added dropwise within 1 hour. The cooling was shut down and the reaction mixture was stirred for another 2.5 hours. Then, water (1.2 ml) was carefully added dropwise to the reaction mixture and the reaction mixture was filtered through a thin layer of celite. Another 35 ml of water were added dropwise to the brightly yellow filtrate under intensive stirring.

후처리

  1. customAt 0-5° C
  2. stirringthe reaction mixture was stirred for another 2.5 hours
  3. filtrationthe reaction mixture was filtered through a thin layer of celite
  4. additionAnother 35 ml of water were added dropwise to the brightly yellow filtrate under intensive stirring

출처 및 근거

ORD 기록
ord-1167146e9d4a4807badd7e70125e4c4c
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034807B2

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