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

HRID 1662952Notes

Reaction equation

HRID 1662952 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1167146e9d4a4807badd7e70125e4c4c
Source dataset
uspto-grants-2011_10
Patent number
US08034807B2

Reaction notes

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