Diisopropylethylamine → 4-bromo-2-fluoro-N-(pyrimidin-2-ylmethyl)benzamide
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:11])[CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[N:14][C:13]=1[CH2:18][NH2:19].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:19][CH2:18][C:13]2[N:14]=[CH:15][CH:16]=[CH:17][N:12]=2)=[O:8])=[C:4]([F:11])[CH:3]=1Participants
6
Procedure
To a flask was charged with 4-bromo-2-fluorobenzoic acid (180 mg, 0.821 mmol), pyrimidin-2-ylmethanamine (89.6 mg, 0.821 mmol), DIEA (0.358 mL, 2.05 mmol) in DMF (3 mL), and to the resulting solution was added PyBOP (513 mg, 0.915 mmol) and the resulting mixture was stirred at room temperature overnight, then was concentrated under reduced pressure and the residue was diluted with EtOAc (20 mL), washed with water (3×10 mL), brine (10 mL) and dried (Na2SO4), concentrated and the residue was purified by flash chromatography on silica gel eluted with gradient EtOAc/heptane (0-100%) and 4-bromo-2-fluoro-N-(pyrimidin-2-ylmethyl)benzamide (74.5 mg, 29.3%) was obtained as light color solid. LCMS (m/z): 310.0/312.0 (MH+), 0.64 min.
Workup
- concentrationwas concentrated under reduced pressure
- additionthe residue was diluted with EtOAc (20 mL)
- washwashed with water (3×10 mL), brine (10 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customthe residue was purified by flash chromatography on silica gel
- washeluted with gradient EtOAc/heptane (0-100%)
Sources & evidence
- ORD record
- ord-bbbb1bd250ff4f17b79b7994733f1a00
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242996B2
Reaction notes
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