Dichloromethane → 1,4-Di(2-fluoro-6-octyloxypyridine-3-yl)benzene

HRID 1780560

반응식

HRID 1780560 반응식
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[F:9][C:10]1[C:15](B(O)O)=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:11]=1.[C:28](=[O:31])([O-])[O-].[Na+].[Na+].ClCCl>C1C=CC=CC=1.C(O)C.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:9][C:10]1[C:15]([C:2]2[CH:7]=[CH:6][C:5]([C:15]3[C:10]([F:9])=[N:11][C:12]([O:31][CH2:28][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])=[CH:13][CH:14]=3)=[CH:4][CH:3]=2)=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:11]=1

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 78041,4-DibromobenzeneHCID 10340Sodium CarbonateHCID 190469402-Fluoro-6-octyloxypyridine-3-boronic acid

생성물 1

HCID 190469471,4-Di(2-fluoro-6-octyloxypyridine-3-yl)benzene수율 79.8%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

0.87 g (3.7 mmol) of 1,4-dibromobenzene, 2.00 g (7.4 mmol) of 2-fluoro-6-octyloxypyridin-3-boronic acid (prepared as described in Example 5), 0.56 g (0.46 mmol) of tetrakis(triphenylphosphine)palladium(0) and 5 g (46.1 mmol) of sodium carbonate in 50 ml of benzene, 35 ml of ethanol and 20 ml of water are refluxed for 18 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, CH2Cl2) and recrystallization from acetonitrile give 1.55 g of 1,4-di(2-fluoro-6-octyloxypyridine-3-yl)benzene. ##STR36##

후처리

  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, CH2Cl2) and recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-a15a2e58252f4142aacc79a69cef98ad
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05630962

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