Water → Tert-butyl[3-(5-bromopyrid-2-yl)phenyl]methylcarbamate

HRID 1092277ノート

反応式

HRID 1092277 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][NH2:15])[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1.CN(C1C=CC=CN=1)C.[C:25](OC([O-])=O)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].O>ClCCl.C(N(CC)CC)C>[C:28]([O:27][C:25](=[O:26])[NH:15][CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH:9]=1)([CH3:31])([CH3:30])[CH3:29]

参加物

7

反応物 4

HCID 962WaterHCID 218852-DimethylaminopyridineHCID 22064466Tert-butyldicarbonateHCID 66591283[3-(5-Bromopyrid-2-yl)phenyl]methylamine

生成物 1

HCID 86664991Tert-butyl[3-(5-bromopyrid-2-yl)phenyl]methylcarbamate収率 81.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
40 °C

実験手順

1.07 g (4 mmol, 1 eq) of [3-(5-bromopyrid-2-yl)phenyl]methylamine are dissolved in 10 mL of dichloromethane in the presence of 1 mL of triethylamine and 200 mg of dimethylaminopyridine. 1.7 g (8 mmol, 2 eq) of tert-butyl dicarbonate are added and the reaction mixture is stirred overnight at 40° C. The reaction is stopped by adding 30 ml of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.18 g of tert-butyl[3-(5-bromopyrid-2-yl)phenyl}methylcarbamate are obtained. Yield=81%.

後処理

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-a8b9c511ae2e4f49a6dd944c3e931eab
出典データセット
uspto-grants-2012_03
特許番号
US08129416B2

反応ノート

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