Triethylamine → 5-bromo-N-[1-(trifluoromethyl)cyclopropyl]pyridine-2-carboxamide

HRID 571543Notes

Reaction equation

HRID 571543 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[F:11][C:12]([F:18])([F:17])[C:13]1([NH2:16])[CH2:15][CH2:14]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:16][C:13]2([C:12]([F:18])([F:17])[F:11])[CH2:15][CH2:14]2)=[O:10])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6085445-Bromopyridine-2-carboxylic acidHCID 116511971-(Trifluoromethyl)cyclopropanamine

Product 1

HCID 709352635-bromo-N-[1-(trifluoromethyl)cyclopropyl]pyridine-2-carboxamideYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromopyridine-2-carboxylic acid (150 mg, 0.74 mmol), 1-(trifluoromethyl)cyclopropanamine (93 mg, 0.74 mmol) (Oakwood, Cat. #: 038175), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (345 mg, 0.780 mmol) and triethylamine (310 μL, 2.2 mmol) in methylene chloride (1 mL) was stirred at room temperature for 3 h. The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-5%) to afford the desired product (124 mg). LCMS (M+H)+: m/z=309.0.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-5%)

Sources & evidence

ORD record
ord-0edf646346e749c7acbcf7b635187f69
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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