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Diisopropylethylamine → 4-bromo-2-fluoro-N-(pyrimidin-2-ylmethyl)benzamide

HRID 595810
Notes
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Reaction equation

HRID 595810 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3026814-Bromo-2-fluorobenzoic acidHCID 2724699PyBOPHCID 46580472-Pyrimidinemethanamine

Product 1

HCID 1180457014-bromo-2-fluoro-N-(pyrimidin-2-ylmethyl)benzamideYield 29.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

  1. concentrationwas concentrated under reduced pressure
  2. additionthe residue was diluted with EtOAc (20 mL)
  3. washwashed with water (3×10 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography on silica gel
  7. washeluted with gradient EtOAc/heptane (0-100%)

Sources & evidence

ORD record
ord-bbbb1bd250ff4f17b79b7994733f1a00
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242996B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes