N-bromobutanimide → 2-(4-Bromo-2-fluorophenylamino)-6-formylaminomethylnicotinic acid methyl ester

HRID 1500680노트

반응식

HRID 1500680 반응식
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]=[O:13])=[N:6][C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Si](C)(C)C)=[CH:17][C:16]=1[F:25].[Br:27]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]=[O:13])=[N:6][C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:27])=[CH:17][C:16]=1[F:25]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 591401742-(2-Fluoro-4-trimethylsilanyl-phenylamino)-6-formylaminomethyl-nicotinic acid methyl ester

생성물 1

HCID 591401622-(4-Bromo-2-fluorophenylamino)-6-formylaminomethylnicotinic acid methyl ester수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-30 °C

실험 절차

To a solution of 2-(2-fluoro-4-trimethylsilanylphenylamino)-6-formylamino methyl-nicotinic acid methyl ester (11.6 g, 30.9 mmol) in DCM (300 mL) at −30° C. was added N-bromo succinimide (5.56 g, 30.9 mmol) portionwise. The reaction mixture was stirred at −30° C. for 30 minutes. The reaction mixture was concentrated in vacuo and the residue partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate. The organic layer was separated and washed with water, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as an orange gum (11.8 g, 100%). LCMS (Method B): RT=3.67 min, M+H+=382/384.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0a1c3fd347084f609106a7f17d41b8fb
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206174B2

반응 노트

불러오는 중…