Stannous chloride dihydrate → [2-Amino-4-(2,4-difluoro-phenylethynyl)-phenyl]-carbamic acid tert.-butyl ester

HRID 1635208Notes

Reaction equation

HRID 1635208 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])=[CH:10][C:9]=1[N+:24]([O-])=O)([CH3:4])([CH3:3])[CH3:2].O.O.Cl[Sn]Cl>>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])=[CH:10][C:9]=1[NH2:24])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69592795[4-(2,4-Difluoro-phenylethynyl)-2-nitro-phenyl]-carbamic acid tert.-butyl ester

Product 1

HCID 69592763[2-Amino-4-(2,4-difluoro-phenylethynyl)-phenyl]-carbamic acid tert.-butyl esterYield 99.9%

Procedure

Prepared from [4-(2,4-difluoro-phenylethynyl)-2-nitro-phenyl]-carbamic acid tert.-butyl ester (Example F11) (750 mg, 2 mmol) by reduction with SnCl2.2H2O (2.26 g, 10 mmol) according to the general procedure G (method b). Obtained as a brown solid (688 mg).

Sources & evidence

ORD record
ord-ba6ec7f03aea4c9894dc5f34b4309f34
Source dataset
uspto-grants-2003_01
Patent number
US06509328B1

Reaction notes

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