1,2-Dimethoxyethane → Methyl 2-[3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-pyridinyl]benzoate

HRID 1007084ノート

反応式

HRID 1007084 の反応式
COCCOC.Br[C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1B(O)O)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[C:8]1[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[O:24])([CH3:21])([CH3:19])[CH3:20]

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 11894Methyl 2-bromobenzoateHCID 10999519(3-(((tert-Butoxycarbonyl)amino)methyl)pyridin-4-yl)boronic acid

生成物 1

HCID 11046130Methyl 2-[3-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-4-pyridinyl]benzoate収率 84%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

20 ml of 1,2-dimethoxyethane were aerated with argon, and 230 mg (0.2 mmol) of Pd(PPh3)4 and 0.86 g (4 mmol) of methyl 2-bromobenzoate were added. After 10 min, 1.51 g (6 mmol) of 3-(tert-butoxycarbonylaminomethyl)pyridine-4-boronic acid and finally 4 ml of a 2M sodium carbonate solution were added. The mixture was heated to reflux under argon for 13 h, diluted with dichloromethane after cooling and washed with water. The organic phase was dried, concentrated and purified by chromatography on silica gel. 1.15 g (84%) of a viscous pale yellow oil were obtained. MS (ES+): m/z=343 (M+1).

後処理

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto reflux under argon for 13 h
  4. temperatureafter cooling
  5. washwashed with water
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel

出典と根拠

ORDレコード
ord-37d854d9b928488c9a0e76ac762d5d53
出典データセット
uspto-grants-2004_09
特許番号
US06794377B2

反応ノート

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