Water → 5-Benzyloxy-2-(4-benzyloxy-phenyl)-1-[4-(3-chloro-propoxy)-benzyl]-3-methyl-1H-indole

HRID 365592Notes

Reaction equation

HRID 365592 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][CH:19]=1)=[C:12]2[CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:35][CH2:36][CH2:37][CH2:38][O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44]Br)=[CH:42][CH:41]=1.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:44][C:43]1[CH:42]=[CH:41][C:40]([O:39][CH2:38][CH2:37][CH2:36][Cl:35])=[CH:47][CH:46]=1)[C:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][CH:19]=1)=[C:12]2[CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 38247451H-Indole, 3-methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-HCID 218822764-(3-Chloropropoxy)-benzyl bromide

Product 1

HCID 121331385-Benzyloxy-2-(4-benzyloxy-phenyl)-1-[4-(3-chloro-propoxy)-benzyl]-3-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution consisting of 5-Benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole No. 7 (6.5 g, 15.5 mmol) in DMF (60 mL) was cooled to 0° C. and treated with addition of sodium hydride (0.68 g, 17.0 mmol) and stirred for 20 minutes. A solution of 4-(3-chloropropoxy)-benzyl bromide No. 163 in DMF (10 mL) was then added slowly. The reaction was allowed to come to rt and stirred for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The ethyl acetate was washed with water, brine and dried over magnesium sulfate and concentrated. The concentrate was treated with methanol and 5 g of the desired product precipitated as a white solid with a melting point of 130-132° C.

Workup

  1. customto come to rt
  2. stirringstirred for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. additionThe concentrate was treated with methanol and 5 g of the desired product
  8. customprecipitated as a white solid with a melting point of 130-132° C.

Sources & evidence

ORD record
ord-86af2fbbee0c4bf2b9bcf5306badb546
Source dataset
uspto-grants-2000_10
Patent number
US06127404

Reaction notes

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