Diisopropylethylamine → N-(3-(1,3,4-oxadiazol-2-yl)phenyl)-4-bromopicolinamide

HRID 389623Notes

Reaction equation

HRID 389623 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.[O:11]1[CH:15]=[N:14][N:13]=[C:12]1[C:16]1[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[O:11]1[CH:15]=[N:14][N:13]=[C:12]1[C:16]1[CH:17]=[C:18]([NH:22][C:8](=[O:10])[C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]=2)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7351504-Bromopyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 162280973-(1,3,4-Oxadiazol-2-yl)aniline

Product 1

HCID 58102932N-(3-(1,3,4-oxadiazol-2-yl)phenyl)-4-bromopicolinamideYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromopyridine-2-carboxylic acid (3.76 g, 18.6 mmol), 3-[1,3,4]oxadiazol-2-yl-phenylamine (3.0 g, 18.6 mmol), (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (7.1 g, 18.7 mmol), and diisopropylethylamine (15 mL) in N,N-dimethylformamide was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, and the residue was stirred with acetonitrile (40 mL) and water (40 mL). The solid thus obtained was isolated by filtration, washed with water (20 mL), acetonitrile (20 mL) and diethyl ether (40 mL), and dried under reduced ressure to give N-(3-(1,3,4-oxadiazol-2-yl)phenyl)-4-bromopicolinamide as a white powder (5.2 g, 15.0 mmol, 81% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe solid thus obtained
  3. customwas isolated by filtration
  4. washwashed with water (20 mL), acetonitrile (20 mL) and diethyl ether (40 mL)
  5. customdried

Sources & evidence

ORD record
ord-b6c13bf4f5f04fbc80369b9d0441b98b
Source dataset
uspto-grants-2013_02
Patent number
US08378108B2

Reaction notes

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