Ethanol → 2-Fluoro-6-octyloxy3-(4-octyloxyphenyl)pyridine

HRID 1780553

反応式

HRID 1780553 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]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1C=CC=CC=1.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.C(OCC)C.O>[F:1][C:2]1[C:7]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:23][CH:22]=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 702EthanolHCID 10340Sodium CarbonateHCID 145298p-Bromophenyl octyl etherHCID 190469402-Fluoro-6-octyloxypyridine-3-boronic acid

生成物 1

HCID 190469692-Fluoro-6-octyloxy3-(4-octyloxyphenyl)pyridine収率 41.5%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 241Benzene溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

2.00 g (7.44 mmol) of 2-fluoro-6-octyloxypyridine-3-boronic acid, 1.64 g (5.72 mmol) of 1-bromo-4-octyloxybenzene, 0.26 g (0.22 mmol) of tetrakis(triphenylphosphine)palladium(0) and 11.16 ml (22.32 mmol) of 2-molar sodium carbonate solution are refluxed in 20 ml of benzene and 10 ml of ethanol for 6 hours. After distributing the reaction mixture between water and diethyl ether, the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography (silica gel, 95:5 hexane/ethyl acetate) and recrystallization from acetonitrile give 1.02 g of 2-fluoro-6-octyloxy3-(4-octyloxyphenyl)pyridine. ##STR23##

後処理

  1. washthe organic phase is washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue
  6. customby chromatography (silica gel, 95:5 hexane/ethyl acetate) and recrystallization from acetonitrile

出典と根拠

ORDレコード
ord-dbb292851d0f40bdbc3c5e9e4eedc4a7
出典データセット
uspto-grants-1997_05
特許番号
US05630962

関連ノート

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