Potassium Carbonate → [6-(4-Cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester

HRID 401573

反応式

HRID 401573 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[C:12]([O:16][C:17](=[O:26])[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](Br)[N:20]=1)([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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:12]([O:16][C:17](=[O:26])[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:20]=1)([CH3:15])([CH3:14])[CH3:13]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 13040380Tert-butyl (6-bromopyridin-2-YL)carbamate

生成物 1

HCID 67133691[6-(4-Cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester収率 60%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21962138N,N-Dimethylformamide--water (1/1)溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-cyanobenzeneboronic acid (7.35 g, 50 mmol), (6-bromo-pyridin-2-yl)carbamic acid tert-butyl ester (13.8 g, 50 mmol), Pd(Ph3P)4 (5.8 g, 0.15 mmol) and K2CO3 (10.4 g, 75 mmol) in DMF/H2O (1:1, 250 mL) was stirred under argon at 80° C. overnight. DMF was evaporated off under reduced pressure and the residue was dissolved in EtOAc (200 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated to dryness. The residue was purified by column (Petroleum Ether/EtOAc 50:1) on silica gel to give [6-(4-cyano-phenyl)-pyridin-2-yl]carbamic acid tert-butyl ester (7.0 g, 60%). 1H NMR (300 MHz, CDCl3) δ 8.02-8.07 (m, 2H), 7.95 (d, J=8.4 Hz, 1H), 7.71-7.79 (m, 3H), 7.37-7.44 (m, 2H), 1.53 (s, 9H).

後処理

  1. customDMF was evaporated off under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc (200 mL)
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column (Petroleum Ether/EtOAc 50:1) on silica gel

出典と根拠

ORDレコード
ord-fff1aa13543d4ff4b374fb4abf25f113
出典データセット
uspto-grants-2014_06
特許番号
US08741933B2

関連ノート

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