Water → Methyl 6-chloro-4-cyano-2-(4-fluoro-3-methylphenylamino)nicotinate

HRID 711451

반응식

HRID 711451 반응식
Cl[C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8]([C:13]#[N:14])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[CH3:23].CCN(CC)CC.O>C(#N)C.CCOC(C)=O>[Cl:12][C:10]1[CH:9]=[C:8]([C:13]#[N:14])[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([F:15])=[C:17]([CH3:23])[CH:18]=2)[N:11]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 679814-Fluoro-m-toluidineHCID 58317683Methyl 2,6-dichloro-4-cyanonicotinate

생성물 1

HCID 58317541Methyl 6-chloro-4-cyano-2-(4-fluoro-3-methylphenylamino)nicotinate

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 2,6-dichloro-4-cyanonicotinate (500 mg, 2.164 mmol), 4-fluoro-3-methylaniline (325 mg, 2.60 mmol) and Et3N (0.452 mL, 3.25 mmol) in ACN (5 mL) was stirred at 50° C. for 24 h. Water and EtOAc were added to the mixture and the aqueous phase was extracted with EtOAc. The organic phases were combined, washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by chromatography on SiO2 to give the title compound, which contains some starting material and was used without further purification (390 mg). [M+H] calc'd for C15H11ClFN3O2, 320. found, 320.

후처리

  1. extractionthe aqueous phase was extracted with EtOAc
  2. washwashed with H2O and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by chromatography on SiO2

출처 및 근거

ORD 기록
ord-331a83e14590484ab21628e242de4e27
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181255B2

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