Diisopropylethylamine → 4-[2-(5-Bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][S:7][CH:6]=1)=[O:4].C(N(C(C)C)C(C)C)C.[Br:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29](O)=[O:30])=[N:25][CH:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:29](=[O:30])[CH2:28][O:27][C:24]2[CH:23]=[CH:22][C:21]([Br:20])=[CH:26][N:25]=2)=[CH:8][S:7][CH:6]=1)=[O:4]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-amino-thiophene-3-carboxylic acid methyl ester (0.5 g, 2.58 mmol) in dimethylformamide (25 mL) was added N-ethyldiisopropylamine (2.25 mL, 12.9 mmol), (5-bromo-pyridin-2-yloxy)-acetic acid ([79674-66-1], 0.6 g, 2.58 mmol) and HATU (Acros 365312, 1.24 g, 3.23 mmol). The reaction mixture was stirred for 2 hours at room temperature. After such time water was added to the reaction mixture until precipitation occurred (sonication was also used to ease precipitation). The precipitate was then isolated by filtration and washed with a mixture of water and ethanol (3:1) to yield the title compound as a light brown solid (0.96 g, 73%).
Workup
- customsonication
- customprecipitation)
- customThe precipitate was then isolated by filtration
- washwashed with a mixture of water and ethanol (3:1)
Sources & evidence
- ORD record
- ord-16aef3cdd3fd46ac85a43084be26b55d
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732452B2
Reaction notes
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