N-bromobutanimide → 3-(3-Bromo-imidazo[1,2-a]pyridine-7-yl)-N-methyl-benzamide

HRID 383304ノート

反応式

HRID 383304 の反応式
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([NH:15][CH3:16])=[O:14])=[CH:6][C:5]=12.C1C(=O)N([Br:27])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:27][C:3]1[N:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=3)[C:13]([NH:15][CH3:16])=[O:14])=[CH:6][C:5]2=[N:1][CH:2]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 684844493-imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide

生成物 1

HCID 684844313-(3-Bromo-imidazo[1,2-a]pyridine-7-yl)-N-methyl-benzamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

3-Imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide (1 eq, 0.398 mmol, 100 mg) is dissolved in DMF (4 ml) at 0° C. and NBS (1.1 eq, 0.438 mmol, 77.9 mg) is added. The reaction mixture is stirred for 1 h at 0° C. and then is diluted with EtOAc. The reaction mixture is washed with NaHCO3 and brine, dried over MgSO4, filtered and evaporated. The product is purified by flash column chromatography eluting with 8:2 DCM/MeOH to afford 3-(3-bromo-imidazo[1,2-a]pyridin-7-yl)-N-methyl-benzamide as a brown solid; [M+H]+=331

後処理

  1. washThe reaction mixture is washed with NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe product is purified by flash column chromatography
  6. washeluting with 8:2 DCM/MeOH

出典と根拠

ORDレコード
ord-9300777925ea4c60acc496568dbdab59
出典データセット
uspto-grants-2013_02
特許番号
US08367662B2

反応ノート

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