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

HRID 1796049ノート

反応式

HRID 1796049 の反応式
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

参加物

6

反応物 2

HCID 693532,5-DibromopyridineHCID 2856454-Fluorophenylboronic acid

生成物 1

HCID 221807795-Bromo-2-(4-fluorophenyl)pyridine収率 88.4%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 10340Sodium Carbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7cf2865dc7b64592a7c48a2c8e137ec7
出典データセット
uspto-grants-2006_04
特許番号
US07030128B2

反応ノート

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