Triethylamine → 1H-indazole-4-carboxylic acid 3-trifluoromethyl-benzylamide
Reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([OH:12])=O)[C:4]=2[CH:3]=[N:2]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[F:53][C:54]([F:64])([F:63])[C:55]1[CH:56]=[C:57]([CH:60]=[CH:61][CH:62]=1)[CH2:58][NH2:59]>CN(C=O)C>[F:53][C:54]([F:63])([F:64])[C:55]1[CH:56]=[C:57]([CH:60]=[CH:61][CH:62]=1)[CH2:58][NH:59][C:10]([C:5]1[C:4]2[CH:3]=[N:2][NH:1][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:12]Participants
6
Procedure
To a stirred room temperature solution of indazole-4-carboxylic acid (1.0 g, 6.1 mmol) in DMF (15 mL) was added PyBOP (3.5 g, 6.5 mmol) and triethylamine (0.90 g, 7.5 mmol). After 15 minutes, 3-trifluoromethyl-benzylamine (1.2 g, 7.0 mmol) was added. After 4 hours, the mixture was quenched with water (30 mL) and diluted with ethyl acetate (20 mL). The organic layer was separated, washed with brine (30 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 20-60% ethyl acetate in hexanes to afford 1H-indazole-4-carboxylic acid 3-trifluoromethyl-benzylamide.
Workup
- waitAfter 4 hours
- customthe mixture was quenched with water (30 mL)
- additiondiluted with ethyl acetate (20 mL)
- customThe organic layer was separated
- washwashed with brine (30 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatography
- washeluting with a gradient of 20-60% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-ac1181225c134ccabbd57594e46d3aa5
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263597B2
Reaction notes
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