2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 67284882, compound

HRID 1618691Notes

Reaction equation

HRID 1618691 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]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([CH3:20])[CH:19]=2)[C:3]=1[CH3:21].[CH3:22][C:23]1([CH3:38])[C:27]2=[N:28][CH:29]=[C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH:31]=[C:26]2[NH:25][CH2:24]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>[CH3:22][C:23]1([CH3:38])[C:27]2=[N:28][CH:29]=[C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH:31]=[C:26]2[N:25]([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]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([CH3:20])[CH:19]=3)[C:3]=2[CH3:21])[CH2:24]1

Participants

7

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 59631296HCID 59631296, compoundHCID 672844994-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholine

Product 1

HCID 67284882HCID 67284882, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y by stirring 4-chloro-5,7-difluoro-3-methyl-2-(5-methylpyridin-3-yl)quinoline (40 mg, 0.131 mmol), 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine (30.6 mg, 0.131 mmol), Pd2dba3 (12.0 mg, 0.013 mmol), XPhos (12.5 mg, 0.026 mmol), sodium tert-butoxide (38 mg, 0.394 mmol), and toluene (1.3 mL) at 105° C. for 2 h. Purification by reverse-phase HPLC (0-60% acetonitrile in water) gave 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methyl-2-(5-methyl-3-pyridinyl)quinoline. 1H NMR (400 MHz, chloroform-d) δ ppm 8.65-8.72 (1H, m), 8.58-8.61 (1H, m), 7.81-7.84 (1H, m), 7.67-7.72 (1H, m), 7.54-7.57 (1H, m), 7.01-7.08 (1H, m), 5.79-5.82 (1H, m), 3.85-3.92 (1H, m), 3.69-3.82 (5H, m), 3.01-3.08 (4H, m), 2.48 (3H, s), 2.32-2.38 (3H, m), 1.67 (3H, br. s.), 1.60 (3H, br. s.). Mass Spectrum (ESI) m/e=502.2 (M+1).

Workup

  1. customPrepared
  2. customPurification by reverse-phase HPLC (0-60% acetonitrile in water)

Sources & evidence

ORD record
ord-3d2f5272182f4ecdb3fe621e5b6df92a
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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