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

HRID 1500680ノート

反応式

HRID 1500680 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0a1c3fd347084f609106a7f17d41b8fb
出典データセット
uspto-grants-2015_12
特許番号
US09206174B2

反応ノート

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