Cesium carbonate → HCID 50940221, compound

HRID 1618634Notes

Reaction equation

HRID 1618634 reaction equation
[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[NH:4][CH2:3]1.Cl[C:19]1[C:28]2[C:23](=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:25]=[CH:26][CH:27]=2)[N:22]=[C:21]([CH3:33])[C:20]=1[CH3:34].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=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]>[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[N:4]([C:19]2[C:28]3[C:23](=[C:24]([C:29]([F:32])([F:30])[F:31])[CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:33])[C:20]=2[CH3:34])[CH2:3]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 672848583,3-Dimethyl-6-morpholinoindolineHCID 67284901HCID 67284901, compound

Product 1

HCID 50940221HCID 50940221, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Prepared according to procedure T using 4-(3,3-dimethylindolin-6-yl)morpholine (0.116 g, 0.5 mmol), 4-chloro-2,3-dimethyl-8-(trifluoromethyl)quinoline (0.19 g, 0.73 mmol), cesium carbonate (0.326 g, 1 mmol), Pd2(dba)3 (0.046 g, 0.05 mmol) and (±) BINAP (0.124 g, 0.2 mmol) were added together in 1,4-dioxane (2 mL). Crude residue was purified via HPLC to give 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2,3-dimethyl-8-(trifluoromethyl)quinoline. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.06 (2H, dd, J=11.3, 8.2 Hz), 7.61 (1H, t, J=7.8 Hz), 7.05 (1H, d, J=8.2 Hz), 6.24 (1H, dd, J=8.2, 2.0 Hz), 5.48 (1H, s), 3.70 (1H, d, J=9.0 Hz), 3.51-3.62 (5H, m), 2.79-2.87 (4H, m), 2.71 (3H, s), 2.23 (3H, s), 1.44 (3H, s), 1.39 (3H, s). Mass Spectrum (ESI) m/e=456 (M+1).

Workup

  1. customPrepared
  2. customCrude residue was purified via HPLC

Sources & evidence

ORD record
ord-f7fe1d4bff264a4a932ad6fb8fe836d0
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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