POTASSIUM DIPHOSPHATE → 5-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole

HRID 1619709笔记

反应方程式

HRID 1619709 反应方程式
Br[C:2]1[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:22][N:23]1[C:27](B(O)O)=[CH:26][CH:25]=[N:24]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:3][C:2]=1[C:27]1[N:23]([CH3:22])[N:24]=[CH:25][CH:26]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参与物

8

反应物 4

HCID 62657POTASSIUM DIPHOSPHATEHCID 75806三环己基膦HCID 111826101-甲基-1H-吡唑-5-硼酸HCID 57535037Benzyl 3-bromobiphenyl-4-yl ether

产物 1

HCID 580422625-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole收率 63.9%

试剂、催化剂与溶剂 3

HCID 9811564三(二亚苄基丙酮)二钯催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 312751,4-二氧六环溶剂

实验过程

A solution of benzyl 3-bromobiphenyl-4-yl ether (500 mg, 1.47 mmol) and (1-methyl-1H-pyrazol-5-yl)boronic acid (185 mg, 1.47 mmol) in dioxane (4 mL) was degassed with argon for 30 minutes. Tris(dibenzylideneacetone)dipalladium (0) (54 mg, 0.06 mmol) and tricyclohexylphosphine (33 mg, 0.12 mmol) were added to the mixture under an argon atmosphere. A degassed solution of tripotassium phosphate (626 mg, 2.95 mmol) in water (2 mL) was added and the mixture was stirred at reflux for 16 hours under an argon atmosphere. The cooled reaction mixture was filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was dissolved in ethyl acetate (25 mL) and the solution was washed with water (2×10 mL), brine (10 mL), dried over Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate in hexane) to afforded the title compound (320 mg).

后处理

  1. temperatureat reflux for 16 hours under an argon atmosphere
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through a pad of Celite
  4. customthe filtrate evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  6. washthe solution was washed with water (2×10 mL), brine (10 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by silica gel column chromatography (10% ethyl acetate in hexane)

来源与证据

ORD记录
ord-3cbad440a0c649e1b2603d2239e95834
来源数据集
uspto-grants-2014_07
专利号
US08772293B2

反应笔记

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