Stannous chloride dihydrate → tert-Butyl {2-amino-4-[(pyridin-2-yl)ethynyl]phenyl}carbamate

HRID 1635194Notes

Reaction equation

HRID 1635194 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][C:9]=1[N+:22]([O-])=O)([CH3:4])([CH3:3])[CH3:2].O.O.Cl[Sn]Cl>>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][C:9]=1[NH2:22])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69592858(2-Nitro-4-pyridin-2-ylethynyl-phenyl)-carbamic acid tert.-butyl ester

Product 1

HCID 69592755tert-Butyl {2-amino-4-[(pyridin-2-yl)ethynyl]phenyl}carbamateYield 54.4%

Procedure

Prepared from (2-nitro-4-pyridin-2-ylethynyl-phenyl)-carbamic acid tert.-butyl ester (Example F8) (262 mg, 0.772 mmol) by reduction with SnCl2.2H2O (871 mg, 3.86 mmol) according to the general procedure G (method b). Obtained as a light brown solid (130 mg).

Sources & evidence

ORD record
ord-95699731bf944d108a6ba9000ef9f747
Source dataset
uspto-grants-2003_01
Patent number
US06509328B1

Reaction notes

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