Trimethylaluminum → 1h-Pyrrolo[2,3-c]pyridine-7-carboxylic acid(4-tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amide

HRID 639530Notes

Reaction equation

HRID 639530 reaction equation
C[Al](C)C.[C:5]([C:9]1[CH:29]=[CH:28][C:12]([CH2:13][NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:18]=2)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].C[O:31][C:32]([C:34]1[N:35]=[CH:36][CH:37]=[C:38]2[CH:42]=[CH:41][NH:40][C:39]=12)=O>ClCCl>[C:5]([C:9]1[CH:29]=[CH:28][C:12]([CH2:13][N:14]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([C:24]([F:26])([F:27])[F:25])[CH:18]=2)[C:32]([C:34]2[N:35]=[CH:36][CH:37]=[C:38]3[CH:42]=[CH:41][NH:40][C:39]=23)=[O:31])=[CH:11][CH:10]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 68563599(4-Tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amineHCID 68576910Methyl 1H-pyrrolo[2,3-C]pyridine-7-carboxylate

Product 1

HCID 247604901h-Pyrrolo[2,3-c]pyridine-7-carboxylic acid(4-tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amideYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trimethylaluminum solution (2 M in heptane, 0.14 mL, 0.28 mmol) was added at RT to a solution of (4-tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amine (100 mg, 0.28 mmol) in dichloromethane (0.7 mL), then after 15 min a solution of 1H-pyrrolo[2,3-c]pyridine-7-carboxylic acid methyl ester (50 mg, 0.14 mmol) in dichloromethane was added. After 2 h the reaction mixture was partitioned between ethyl acetate and 2 M aq. hydrochloric acid solution. The organic layer was washed with brine, dried (MgSO4), evaporated, and chromatographed (SiO2, heptane/ethyl acetate gradient), to afford the title compound (70 mg, 50%). White foam, MS (ISP) 498.3 (M+H)+.

Workup

  1. customAfter 2 h the reaction mixture was partitioned between ethyl acetate and 2 M aq. hydrochloric acid solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customchromatographed (SiO2, heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-27a51ddfda504665931eea5c457611d3
Source dataset
uspto-grants-2010_04
Patent number
US07691876B2

Reaction notes

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