三氯甲烷 → 2-tert-butyl-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-phenyl-1H-indole-7-carbonitrile

HRID 17536

反应方程式

HRID 17536 反应方程式
[NH2:1][C:2]1[C:7]([C:8]#[C:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[C:6]([N:14]2[CH2:18][CH2:17][C@H:16]([N:19]([CH3:21])[CH3:20])[CH2:15]2)[C:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:4][C:3]=1[C:28]#[N:29].C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(#N)C.CC#N.CC#N.Cl[Pd]Cl>[C:10]([C:9]1[NH:1][C:2]2[C:7]([CH:8]=1)=[C:6]([N:14]1[CH2:18][CH2:17][C@H:16]([N:19]([CH3:21])[CH3:20])[CH2:15]1)[C:5]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:4][C:3]=2[C:28]#[N:29])([CH3:13])([CH3:11])[CH3:12]

参与物

6

反应物 3

HCID 6212三氯甲烷HCID 516892碳酸氢钠HCID 866308714-Amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-(3,3-dimethylbutyn-1-yl)biphenyl-3-carbonitrile

产物 1

HCID 685851312-tert-butyl-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-phenyl-1H-indole-7-carbonitrile收率 60%

试剂、催化剂与溶剂 2

HCID 6093782双(乙腈)氯化钯(II)催化剂HCID 6342乙腈溶剂

实验过程

4-Amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-(3,3-dimethylbutyn-1-yl)biphenyl-3-carbonitrile (I-246) (54 mg, 0.14 mmol) was dissolved in acetonitrile (3 ml), and at room temperature, bis(acetonitrile)palladium(II) dichloride (7.3 mg, 0.28 mmol) was added, followed by heating under reflux for 3 hours. After cooling to room temperature, the reaction liquid was fractionated with chloroform and an aqueous saturated sodium hydrogencarbonate solution. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=95:5) to obtain a crude product of the entitled compound (32 mg, 60%) as a pale brown gel. This was recrystallized from hexane/diethyl ether to obtain the entitled compound (15 mg) as a pale brown powder.

后处理

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. customthe reaction liquid
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=95:5)

来源与证据

ORD记录
ord-0ca3847f243b437983c3d219f6ea998b
来源数据集
uspto-grants-2010_06
专利号
US07737166B2

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