2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 67285611, compound

HRID 1618671Notes

Reaction equation

HRID 1618671 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([N:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:3]=1[CH3:28].[CH3:29][C:30]1([CH3:45])[C:34]2=[N:35][CH:36]=[C:37]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[CH:38]=[C:33]2[NH:32][CH2:31]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC(C)([O-])C.[Na+]>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].C1(C)C=CC=CC=1>[CH3:29][C:30]1([CH3:45])[C:34]2=[N:35][CH:36]=[C:37]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[CH:38]=[C:33]2[N:32]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=3[F:12])[N:5]=[C:4]([N:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:3]=2[CH3:28])[CH2:31]1

Participants

7

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 672844994-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholineHCID 67285315HCID 67285315, compound

Product 1

HCID 67285611HCID 67285611, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y by stirring tert-butyl 4-chloro-5,7-difluoro-3-methylquinolin-2-yl(pyridin-2-yl)carbamate (100 mg, 0.246 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (57.5 mg, 0.246 mmol), Pd2dba3 (22.6 mg, 0.025 mmol), XPhos (23.5 mg, 0.049 mmol), sodium tert-butoxide (71.0 mg, 0.739 mmol), and toluene (2.5 mL) at 100° C. for 30 min. Purification by column chromatography on silica gel (0-60% EtOAc in hexanes) gave tert-butyl 4-(3,3-dimethyl-6-morpholino-2,3-dihydro-1H-pyrrolo[3,2-b]-pyridin-1-yl)-5,7-difluoro-3-methylquinolin-2-yl(pyridin-2-yl)carbamate. Mass Spectrum (ESI) m/e=603.2 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography on silica gel (0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ea97f225ea1e402281b34d23d7c7f9b2
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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