N,N-二异丙基乙胺 → 4-[3-(2,4-Dichloro-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075673笔记

反应方程式

HRID 2075673 反应方程式
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6](I)=[CH:7][CH:8]=2)[N:3]=1.[SH:14][C:15]1[CH:16]=[C:17]([C:21]2([C:27]#[N:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1.CCN(C(C)C)C(C)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.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]>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([S:14][C:15]3[CH:16]=[C:17]([C:21]4([C:27]#[N:28])[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[CH:18]=[CH:19][CH:20]=3)=[CH:7][CH:8]=2)[N:3]=1

参与物

7

反应物 4

HCID 81531N,N-二异丙基乙胺HCID 6360444,5-双二苯基膦-9,9-二甲基氧杂蒽HCID 187863864-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrileHCID 866138212,4-Dichloro-7-iodo-quinoline

产物 1

HCID 866138254-[3-(2,4-Dichloro-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

试剂、催化剂与溶剂 2

HCID 9811564三(二亚苄基丙酮)二钯催化剂HCID 312751,4-二氧六环溶剂

反应条件

温度
60 °C

实验过程

2,4-Dichloro-7-iodo-quinoline (3.4 g, 10.5 mmol), 4-(3-mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (3a, 2.3 g, 10.5 mmol), iPr2NEt (3.67 mL, 21.0 mmol), Pd2dba3 (240 mg, 0.26 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (303 mg, 0.52 mmol) were dissolved in 1,4-dioxane (50 mL) and degassed for 10 minutes with N2. The reaction was then sealed and heated to 60° C. for 1 hour. After cooling to room temperature, the reaction was diluted with EtOAc and saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentration. The residue was purified by silica gel chromatography (30% EtOAc in hexanes) to give the desired product, 3b.

后处理

  1. customdegassed for 10 minutes with N2
  2. customThe reaction was then sealed
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction was diluted with EtOAc and saturated aqueous NH4Cl
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentration
  9. customThe residue was purified by silica gel chromatography (30% EtOAc in hexanes)

来源与证据

ORD记录
ord-f7cf6a8aff294b7da929f79cd5125135
来源数据集
uspto-grants-2011_04
专利号
US07919621B2

反应笔记

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