Diisopropylethylamine → 4-bromo-N-(4-isopropyl-3-methylphenyl)picolinamide

HRID 2283474ノート

反応式

HRID 2283474 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10]C)=O)[CH:3]=1.Cl.[CH:13]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[CH3:23])([CH3:15])[CH3:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([CH:13]([CH3:14])[CH3:15])=[C:17]([CH3:23])[CH:18]=2)=[O:10])[CH:3]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 27962704-Isopropyl-m-toluidinium chlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12828947Methyl 4-bromopicolinate

生成物 1

HCID 1182507534-bromo-N-(4-isopropyl-3-methylphenyl)picolinamide収率 80%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of methyl 4-bromopicolinate (1.0 g, 5.0 mmol) in DCM (500 mL) and DMF (20 mL) was added 4-isopropyl-3-methylbenzenamine hydrochloride (1.08 g, 5.90 mmol), HATU (3.8 g, 10 mmol), DIPEA (4.9 mL, 30 mmol) and the mixture was stirred at reflux overnight. After cooling to room temperature and evaporation of the solvent, the residue was purified by combi-flash (ISCO, 40g silica, UV254, 3:1 pet ether/ethyl acetate) to afford 4-bromo-N-(4-isopropyl-3-methylphenyl)picolinamide (1.32 g, 80% yield) as a yellow oil: MS (ES) m/z 333 (M+H).

後処理

  1. temperatureat reflux overnight
  2. customevaporation of the solvent
  3. customthe residue was purified by combi-flash (ISCO, 40g silica, UV254, 3:1 pet ether/ethyl acetate)

出典と根拠

ORDレコード
ord-f777dd1fb7934bd5871f4b96b378eeb3
出典データセット
uspto-grants-2015_09
特許番号
US09145393B2

反応ノート

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