Triethylamine → 4-Bromo-6-fluoro-1-[4-(phenylmethoxy)phenyl]-1H-indole

HRID 2421243Notes

Reaction equation

HRID 2421243 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343144-Benzyloxy-phenylboronic acidHCID 247281734-Bromo-6-fluoro-1H-indole

Product 1

HCID 596279334-Bromo-6-fluoro-1-[4-(phenylmethoxy)phenyl]-1H-indoleYield 55.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromo-6-fluoro-1H-indole (D16), (200 mg, 0.935 mmol), 4-benzyloxyphenylboronic acid (426 mg, 1.87 mmol), copper (II) acetate (332 mg, 1.87 mmol) and triethylamine (0.26 mL, 188 mg, 1.87 mmol) in dichloromethane (5 mL) was stirred in air at room temperature for 16 hours. The mixture was filtered through celite, concentrated and purified by chromatography on silica gel (elution with 0-20% ethyl acetate in hexanes) to give the title compound as a pink solid (D19), (205 mg).

Workup

  1. filtrationThe mixture was filtered through celite,
  2. concentrationconcentrated
  3. custompurified by chromatography on silica gel (elution with 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-de9a19f1079c4412a44be83ebc2aaa53
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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