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

HRID 574119

반응식

HRID 574119 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 8176802,5-Dibromo-3-methylpyridineHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 207750075-Bromo-3-methylpyridine-2-carbonitrile수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-be185d5d29fe41168b38af8effef2105
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034870B2

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