Trimethylaluminum → N-(2,3-dihydrobenzoxazin-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 225801Notes

Reaction equation

HRID 225801 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][NH:9][CH2:8][CH2:7][C:6]=2[CH:11]=1.C[Al](C)C.[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1)[C:21]([C:34](OCC)=[O:35])=[CH:20]2>>[O:10]1[C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:34]([C:21]3[N:22]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=4)[C:23]4[C:19]([CH:20]=3)=[CH:18][C:17]([F:16])=[CH:25][CH:24]=4)=[O:35])=[CH:11][C:6]=2[CH2:7][CH2:8][NH:9]1

Participants

4

Reactant 3

HCID 16682925TrimethylaluminumHCID 57431514Ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylateHCID 666930296-Amino-2,3-dihydrobenzoxazine

Product 1

HCID 68529616N-(2,3-dihydrobenzoxazin-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamideYield 29.2%

Procedure

The process is performed according to the method described in Example 6, starting with 0.090 g of 6-amino-2,3-dihydrobenzoxazine (WO 2003/049702), 0.5 ml of trimethylaluminum (2M in toluene) and 0.157 g of ethyl 5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylate, obtained in step 1.1 of Example 1. 0.061 g of product is obtained.

Workup

  1. customobtained in step 1.1 of Example 1

Sources & evidence

ORD record
ord-67a5489fec274f3fbdac13592286c601
Source dataset
uspto-grants-2009_07
Patent number
US07557134B2

Reaction notes

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