Sodium Bicarbonate → 2-[(Aminocarbonyl)amino]-5-[4-formylphenyl]thiophene-3-carboxamide

HRID 2421365Notes

Reaction equation

[NH2:1][C:2]([NH:4][C:5]1[S:6][C:7](Br)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3].C(=O)(O)[O-].[Na+].[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20]>COCCOC>[NH2:1][C:2]([NH:4][C:5]1[S:6][C:7]([C:24]2[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11])=[O:3]

Participants

Conditions

Temperature: 90 °C

Procedure

2-[(Aminocarbonyl)amino]-5-bromo-3-thiophenecarboxamide (11.75 g) was stirred in 1,2-dimethoxyethane (500 ml) and saturated aqueous sodium bicarbonate solution (100 ml), and 4-formylphenyl boronic acid (10 g) was added. The flask was flushed with argon, and tetrakis-(triphenylphosphine)palladium(0) (5.1 g) was then added. The reaction was stirred at 90° C. for 2 h, then cooled and evaporated under reduced pressure. The residue was treated with dichloromethane (200 ml) and 2N sodium hydroxide solution (100 ml), and stirred for twenty minutes. The resulting solid was then isolated by filtration, and purified by trituration with ethanol (100 ml), giving the product as a pale green solid (5.75 g).

Workup

customThe flask was flushed with argon, and tetrakis-(triphenylphosphine)palladium(0) (5.1 g)
additionwas then added
temperaturecooled
customevaporated under reduced pressure
additionThe residue was treated with dichloromethane (200 ml) and 2N sodium hydroxide solution (100 ml)
stirringstirred for twenty minutes
customThe resulting solid was then isolated by filtration
custompurified by trituration with ethanol (100 ml)

Sources & evidence

ORD record: ord-d7e486f5e18542af9f6aef0dce52cfe6
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956084B2

Reaction notes

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