Cesium carbonate → HCID 67345213, compound

HRID 1029030Notes

Reaction equation

HRID 1029030 reaction equation
[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:27](Cl)=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])[CH:8]=2)[N:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:69][C:70]([CH3:74])([CH3:73])[C:71]#[CH:72]>CC#N.CC#N.Cl[Pd]Cl>[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:27]([C:72]#[C:71][C:70]([CH3:74])([CH3:73])[CH3:69])=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])[CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 135123,3-Dimethyl-1-butyneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67348768HCID 67348768, compound

Product 1

HCID 67345213HCID 67345213, compound

Reagents, catalysts & solvents 1

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalyst

Procedure

A vial was charged with methyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-chlorobenzoate (841 mg, 2.114 mmol), dichlorobis(acetonitrile)palladium(II) (54.8 mg, 0.211 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (302 mg, 0.634 mmol) and cesium carbonate (1.79 g, 5.50 mmol). The vial was evacuated and backfilled with nitrogen gas 3×. ACN (9 mL) was added and the suspension was allowed to stir at RT for 20 min. 3,3-Dimethyl-1-butyne (0.521 mL, 4.23 mmol) was added and the reaction mixture was heated to 90° C. for 3.5 h. The reaction mixture was partitioned between water and EtOAc. The organic phase was separated and dried over MgSO4. The solvent was removed under reduce pressure and the remaining residue was purified by column chromatography (10% MeOH in DCM). Methyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-(3,3-dimethylbut-1-ynyl)benzoate was obtained as an orange-brown solid.

Workup

  1. customThe vial was evacuated
  2. additionACN (9 mL) was added
  3. temperaturethe reaction mixture was heated to 90° C. for 3.5 h
  4. customThe reaction mixture was partitioned between water and EtOAc
  5. customThe organic phase was separated
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed
  8. customthe remaining residue was purified by column chromatography (10% MeOH in DCM)

Sources & evidence

ORD record
ord-0981476433fb4a00bfabb20e82bb3cbd
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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