2,5-Dibromopyridine → 5-Bromo-2-(4-fluorophenyl)pyridine

HRID 1796049노트

반응식

HRID 1796049 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].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>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)=[N:3][CH:4]=1

참가 물질

6

반응물 2

HCID 693532,5-DibromopyridineHCID 2856454-Fluorophenylboronic acid

생성물 1

HCID 221807795-Bromo-2-(4-fluorophenyl)pyridine수율 88.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

실험 절차

To a degassed mixture of 2,5-dibromopyridine (500 mg, 2.11 mmol) and 4-fluorobenzeneboronic acid (444 mg, 3.17 mmol) in ethylene glycol dimethyl ether (4.2 ml) and 2M aqueous sodium carbonate (2.1 ml) was added tetrakis(triphenylphosphine)palladium(0) (98 mg, 0.08 mmol). This mixture was heated at reflux for 14 h. After cooling the crude reaction was partitioned between water and dichloromethane. The organics were dried over anhydrous magnesium sulfate, filtered and adsorbed onto silica. Purification by chromatography on silica gel, eluting with a mixture of 4% diethyl ether in isohexane, gave 5-bromo-2-(4-fluorophenyl)pyridine (470 mg) as a white solid: δH (360 MHz, CDCl3) 7.30 (1H, d, J 7), 7.12-7.19 (2H, m), 7.57 (1H, d, J 8), 7.86 (1H, dd, J 2 and 8), 7.92-7.98 (2H, m), 8.72 (1H, d, J 2), m/z (ES+) 251, 252, 253, 254 (M++H).

후처리

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 14 h
  3. temperatureAfter cooling the crude
  4. customreaction
  5. customwas partitioned between water and dichloromethane
  6. dry with materialThe organics were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customPurification by chromatography on silica gel
  9. washeluting with a mixture of 4% diethyl ether in isohexane

출처 및 근거

ORD 기록
ord-7cf2865dc7b64592a7c48a2c8e137ec7
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030128B2

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