Dimethylformamide → 5-Bromo-N-cyclopropylpyridine-2-carboxamide

HRID 557882

反応式

HRID 557882 の反応式
C([N:4](CC)[CH:5]([CH3:7])[CH3:6])(C)C.[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:19])=O)=[N:15][CH:16]=1.C1(N)CC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O>C(OCC)(=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([NH:4][CH:5]2[CH2:7][CH2:6]2)=[O:19])=[N:15][CH:16]=1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6085445-Bromopyridine-2-carboxylic acid

生成物 1

HCID 263700895-Bromo-N-cyclopropylpyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

N,N-Diisopropylethylamine (0.69 mL, 0.0040 mol) was added to a mixture of 5-bromopyridine-2-carboxylic acid (400 mg, 0.002 mol), cyclopropylamine (0.16 mL, 0.0024 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.1 g, 0.0024 mol) in N,N-dimethylformamide (9.4 mL, 0.12 mol) at 0° C. and the mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate, washed with water and brine successively, dried over sodium sulfate, filtered and concentrated. The product was purified by CombiFlash eluting with CH2Cl2/EtOAc (max.EtOAc 20%). LC-MS: 241.1/243.1 (M+H+)

後処理

  1. washwashed with water and brine successively
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by CombiFlash
  6. washeluting with CH2Cl2/EtOAc (max.EtOAc 20%)

出典と根拠

ORDレコード
ord-608f3976613242cc85a4cb23aedc7b10
出典データセット
uspto-grants-2011_11
特許番号
US08058288B2

関連ノート

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