Dichloromethane → 2-Fluoro-6-octyloxy-3-[4-(4-octyloxyphenyl)phenyl]pyridine

HRID 1780559

反応式

HRID 1780559 の反応式
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[C:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>C(O)C.C1C=CC=CC=1.O.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>[F:1][C:2]1[C:7]([C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:31][CH:32]=3)=[CH:25][CH:26]=2)=[CH:6][CH:5]=[C:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:3]=1

参加物

9

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 28017871-Bromo-4-(4-octoxyphenyl)benzeneHCID 190469402-Fluoro-6-octyloxypyridine-3-boronic acid

生成物 1

HCID 190469732-Fluoro-6-octyloxy-3-[4-(4-octyloxyphenyl)phenyl]pyridine収率 13.2%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 241Benzene溶媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

2.10 g (7.50 mmol) of 2-fluoro-6-octyloxypyridine-3-boronic acid (prepared as described in Example 5) in 35 ml of ethanol are refluxed together with 2.70 g (7.50 mmol) of 4-bromo-4'-octyloxybiphenyl and 0.29 g (0.24 mmol) of tetrakis(triphenylphosphine)palladium in 46 ml of benzene and 2.5 g (23.40 mmol) of sodium carbonate in 11 ml of water for 20 hours. After distributing the reaction mixture between water and dichloromethane, the organic phase is washed with sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography (silica gel, dichloromethane) and recrystallization from acetonitrile give 0.50 g of 2-fluoro-6-octyloxy-3-[4-(4-octyloxyphenyl)phenyl]pyridine. ##STR32##

後処理

  1. washthe organic phase is washed with sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue
  6. customby chromatography (silica gel, dichloromethane) and recrystallization from acetonitrile

出典と根拠

ORDレコード
ord-51874d2e1e3549caa257c4049dcb364b
出典データセット
uspto-grants-1997_05
特許番号
US05630962

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