Diisopropylethylamine → 1-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid (6-bromo-pyridin-3-ylmethyl)-amide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17](Cl)=[O:18])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[Br:20][C:21]1[N:26]=[CH:25][C:24](NC)=[CH:23][CH:22]=1.C[CH2:30][N:31](C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:20][C:21]1[N:26]=[CH:25][C:24]([CH2:30][NH:31][C:17]([C:12]2[C:11]3[CH:10]=[N:9][N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[C:16]=3[CH:15]=[CH:14][CH:13]=2)=[O:18])=[CH:23][CH:22]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid chloride (416 mg, 1.51 mmol), 6-bromo-pyridin-3-yl-methylamine (311 mg, 1.66 mmol) and DMAP (18.5 mg, 0.151 mmol) in DCM (10 mL) was treated with DIEA (1.32 mL, 7.56 mmol). The solution was stirred at room temperature. After 16 hours the mixture was diluted with DCM (30 mL). The organic layer was washed with saturated aqueous NH4Cl (2×10 mL), saturated aqueous NaHCO3 (2×10 mL), water (10 mL), brine (10 mL) and dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-50% ethyl acetate in hexanes to afford the title compound as a white solid.
Workup
- washThe organic layer was washed with saturated aqueous NH4Cl (2×10 mL), saturated aqueous NaHCO3 (2×10 mL), water (10 mL), brine (10 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography
- washeluting with a gradient of 0-50% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-b1b6ee2a75bb4f14b519d4c3fb808a17
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008327B2
Reaction notes
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