Potassium Carbonate → HCID 10285978、化合物

HRID 2099512ノート

反応式

HRID 2099512 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:19]1[N:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][CH:20]=1>CN(C=O)C.CCOC(C)=O>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[CH:5]=[N:1][N:2]([C:19]2[N:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][CH:20]=2)[CH:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 35789812-(1H-pyrazol-4-yl)pyridineHCID 142963696-Fluoropyridine-2-carbonitrile

生成物 1

HCID 10285978HCID 10285978、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

2-(1H-Pyrazol-4-yl)pyridine (300 mg, 2.0 mmol) was dissolved in DMF (10 mL), potassium carbonate (566 mg, 4 mmol) and 6-fluoropyridine-2-carbonitrile (250 mg, 2 mmol) was added. The reaction was heated at 140° C. for 16 h. The crude mixture was cooled to rt and diluted with EtOAc (300 mL) and washed with H2O (200 mL) and brine (200 mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexanes:EtOAc (7:3) to afford 6-(4-pyridin-2-yl-1H-pyrazol-1-yl)pyridine-2-carbonitrile. This material was dissolved in methylene chloride (5 mL) and, upon treatment with 1M HCl in diethyl ether (0.6 mL), precipitated as the hydrochloride salt. M.P. 260-261° C. 1H-NMR (CDCl3, 300 MHz) δ 9.67 (s, 1H), 8.83 (s, 1H), 8.79-8.77 (d, J=6 Hz, 1H), 8.47-8.29 (m, 4H), 8.13-8.10 (m, 1H) 7.77-7.73 (t, 1H). MS ESI) 249 (M++H).

後処理

  1. washwashed with H2O (200 mL) and brine (200 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with hexanes:EtOAc (7:3)

出典と根拠

ORDレコード
ord-0dfc75360f684ecba5516dbb27d38ce3
出典データセット
uspto-grants-2009_08
特許番号
US07569592B2

反応ノート

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