1H-Indole-7-carboxylic acid → 1H-indole-7-carboxylic acid (4-tert-butyl-2-hydroxy-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide

HRID 855248Notes

Reaction equation

HRID 855248 reaction equation
CCN=C=NCCCN(C)C.Cl.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[C:22]([OH:24])=O)[CH:15]=[CH:14]1.[C:25]([C:29]1[CH:30]=[CH:31][C:32]([CH2:36][NH:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)=[C:33]([OH:35])[CH:34]=1)([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([C:29]1[CH:30]=[CH:31][C:32]([CH2:36][N:37]([CH2:38][CH2:39][C:40]2[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=2)[C:22]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:21]=2[NH:13][CH:14]=[CH:15]3)=[O:24])=[C:33]([OH:35])[CH:34]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 742811H-Indole-7-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 693423465-Tert-butyl-2-{[2-(4-fluoro-phenyl)-ethylamino]-methyl}-phenol

Product 1

HCID 866030371H-indole-7-carboxylic acid (4-tert-butyl-2-hydroxy-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.69 g (8.8 mmol) of EDC.HCl were added to 1.46 g (8.8 mmol) of 1H-indol-7-carboxylic acid and 2.41 g (8.8 mmol) of 5-tert-butyl-2-{[2-(4-fluoro-phenyl)-ethylamino]-methyl}-phenol dissolved in 80 ml DCM. The reaction mixture was stirred at rt over night, diluted with DCM and washed once with water and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (250 g silica gel; heptane/EtOAc 7:3) to yield 2.9 g (82%) 1H-indole-7-carboxylic acid (4-tert-butyl-2-hydroxy-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide as a colorless foam. MS (ISP) 445.3 (M+H)+.

Workup

  1. washwashed once with water and once with saturated aqueous NaCl solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was purified by column chromatography (250 g silica gel; heptane/EtOAc 7:3)

Sources & evidence

ORD record
ord-64323683dbaa4314b418e0680cb74bff
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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