Cesium carbonate → HCID 67285088, compound

HRID 1618619Notes

Reaction equation

HRID 1618619 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](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[CH:21][C:20]=1[CH3:29].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>C1(C)C=CC=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.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](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[CH:21][C:20]=2[CH3:29])[CH2:3]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2568884-chloro-3-methylquinolineHCID 634876Binap, (A+-)-HCID 672848583,3-Dimethyl-6-morpholinoindoline

Product 1

HCID 67285088HCID 67285088, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure T using 4-(3,3-dimethylindolin-6-yl)morpholine (0.175 g, 0.754 mmol), 4-chloro-3-methylquinoline (0.134 g, 0.754 mmol), cesium carbonate (0.492 g, 1.5 mmol), Pd2(dba)3 (0.069 g, 0.075 mmol) and (±) BINAP (0.070 g, 0.113 mmol) in toluene (3 mL). After purification by HPLC 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-3-methylquinoline was obtained. 1H NMR (400 MHz, MeOH) δ ppm 8.82 (1H, s), 8.07 (1H, d, J=8.2 Hz), 7.94 (1H, d, J=8.2 Hz), 7.73 (1H, m), 7.55 (1H, t, J=7.6 Hz), 7.10 (1H, d, J=8.2 Hz), 6.39 (1H, dd, J=8.2, 2.0 Hz), 5.59 (1H, s), 3.79 (1H, m), 3.76 (1H, m), 3.68 (4H, m), 2.89 (4H, m), 2.37 (3H, s), 1.50 (3H, s), 1.46 (3H, s). Mass Spectrum (ESI) m/e=375 (M+1).

Workup

  1. customPrepared
  2. customAfter purification by HPLC 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-3-methylquinoline
  3. customwas obtained

Sources & evidence

ORD record
ord-d603d97b64a84a178d32d761c70ef51a
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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