Potassium Carbonate → HCID 57824433、化合物

HRID 1192803ノート

反応式

HRID 1192803 の反応式
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[F:16][C:17]([F:29])([F:28])[O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>CCOCC.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>[F:16][C:17]([F:28])([F:29])[O:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[N:7]=[C:6]([C:8]3[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 110762394-(6-Bromopyridin-2-yl)benzaldehyde

生成物 1

HCID 57824433HCID 57824433、化合物収率 75.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 3283Diethyl Ether溶媒

実験手順

4-(6-Bromo-pyridin-2-yl)-benzaldehyde (0.31 mmol), 4-trifluoromethoxyphenyl boronic acid (0.46 mmol), tetrakis(triphenylphosphine)palladium(0) (0.003 mmol), 2 M potassium carbonate (0.31 mL) and dioxane (2 mL) were combined in a vial and irradiated by microwave for 10 min at 150° C. The reaction mixture was taken up in ether and washed with brine. The organic layer was dried over magnesium sulfate, was filtered and the solvent removed in vacuo. Purification by silica gel chromatography (EtOAc/hexanes) yielded the product (80 mg) as an off-white solid: mp 109-112° C.; 1H NMR (400 MHz, CDCl3) δ 10.11 (s, 1H), 8.32 (d, J=8.5 Hz, 2H), 8.19 (d, J=8.1 Hz, 2H), 8.03 (d, J=8.4 Hz, 2H), 7.89 (t, J=7.9 Hz, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.74 (d, J=8.0 Hz, 1H), 7.35 (d, J=8.3 Hz, 2H); EIMS m/z 343 (M+).

後処理

  1. customirradiated by microwave for 10 min at 150° C
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationwas filtered
  5. customthe solvent removed in vacuo
  6. customPurification by silica gel chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-30a0d6283bd44a048cb6ed0e1785097a
出典データセット
uspto-grants-2014_03
特許番号
US08680269B2

反応ノート

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