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

HRID 2283474노트

반응식

HRID 2283474 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f777dd1fb7934bd5871f4b96b378eeb3
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145393B2

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