Water → 5-Bromo-3-methylpyridine-2-carbonitrile

HRID 574119

反応式

HRID 574119 の反応式
[Cu][C:2]#[N:3].Br[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][N:6]=1.O>CN(C=O)C>[Br:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:2]#[N:3])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 962WaterHCID 8176802,5-Dibromo-3-methylpyridineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 207750075-Bromo-3-methylpyridine-2-carbonitrile収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Copper(I) cyanide (21 g, 0.24 mol) was added to a solution of 2,5-dibromo-3-methylpyridine (49, 60 g, 0.24 mol) in dry DMF (200 mL), and the mixture was heated at reflux for 2 h. After cooling to room temperature, water (1500 mL) was added to the mixture and the products were extracted with ethyl acetate (3×300 mL). The combined extracts were washed with water (3×300 mL), brine (300 mL), dried with sodium sulfate and evaporated to dryness. The brown oily residue was subjected to flash column chromatography (silica gel), eluting with chloroform, to yield 50 as a white solid (35 g, 74%): mp 86-88° C. 1H NMR (300 MHz, CDCl3) δ 8.55 (d, J=1.8 Hz, 1H), 7.84 (d, J=1.5 Hz, 1H), 2.53 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 149.75, 140.68, 139.95, 132.25, 124.61, 115.90, 18.59; EIMS m/z 196/198 (M+); CIMS 197/199 (MH+). The 1H NMR spectrum is consistent with previously published data (Bioorg. Med. Chem. 1999, 7, 1845-1855).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. extractionthe products were extracted with ethyl acetate (3×300 mL)
  4. washThe combined extracts were washed with water (3×300 mL), brine (300 mL)
  5. dry with materialdried with sodium sulfate
  6. customevaporated to dryness
  7. washeluting with chloroform

出典と根拠

ORDレコード
ord-be185d5d29fe41168b38af8effef2105
出典データセット
uspto-grants-2015_05
特許番号
US09034870B2

関連ノート

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