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

HRID 225802Notes

Reaction equation

HRID 225802 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][NH:9][C:8](=[O:11])[CH2:7][C:6]=2[CH:12]=1.C[Al](C)C.[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=1)[C:22]([C:35](OCC)=[O:36])=[CH:21]2>>[O:11]=[C:8]1[CH2:7][C:6]2[CH:12]=[C:2]([NH:1][C:35]([C:22]3[N:23]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=4)[C:24]4[C:20]([CH:21]=3)=[CH:19][C:18]([F:17])=[CH:26][CH:25]=4)=[O:36])[CH:3]=[CH:4][C:5]=2[O:10][NH:9]1

Participants

4

Reactant 3

HCID 16682925TrimethylaluminumHCID 222790776-amino-3-oxo-2H-benzoxazineHCID 57431514Ethyl 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylate

Product 1

HCID 68534223N-(3-oxo-2H-benzoxazin-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamideYield 24.6%

Procedure

The process is performed according to the method described in Example 6, starting with 0.107 g of 6-amino-3-oxo-2H-benzoxazine (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. 0.053 g of product is obtained.

Workup

  1. customobtained in step 1.1 of Example 1

Sources & evidence

ORD record
ord-4c3b966fb76344cab04e0f3cb7c773b0
Source dataset
uspto-grants-2009_07
Patent number
US07557134B2

Reaction notes

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