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

HRID 1245843Notes

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-045b2bf8eb414c9ba0ace49b4251d090
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125896B2

Reaction notes

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