Cesium carbonate → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2-(2-fluorophenyl)-3-methylquinoline

HRID 1618627Notes

Reaction equation

HRID 1618627 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]=[C:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])[C:20]=1[CH3:36].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](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[C:20]=2[CH3:36])[CH2:3]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 596311684-Chloro-2-(2-fluorophenyl)-3-methylquinolineHCID 672848583,3-Dimethyl-6-morpholinoindoline

Product 1

HCID 509401104-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2-(2-fluorophenyl)-3-methylquinoline

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 (0.043 g, 0.184 mmol), 4-chloro-2-(2-fluorophenyl)-3-methylquinoline (0.050 g, 0.184 mmol), cesium carbonate (0.12 g, 0.368 mmol), Pd2(dba)3 (0.017 g, 0.018 mmol) and (±) BINAP (0.0174 g, 0.028 mmol) in 1,4-dioxane (1 mL). After purification by HPLC 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2-(2-fluorophenyl)-3-methylquinoline was obtained. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.00 (1H, d, J=7.8 Hz), 7.82 (1H, d, J=8.2 Hz), 7.69 (1H, t, J=7.6 Hz), 7.52 (3H, m), 7.30 (2H, m), 6.98 (1H, d, J=8.2 Hz), 6.20 (1H, dd, J=8.2, 2.0 Hz), 5.46 (1H, d, J=2.0 Hz), 3.75 (1H, d, J=9.0 Hz), 3.60 (1H, d, J=9.4 Hz), 3.51 (4H, m), 2.77 (4H, m), 1.99 (3H, s), 1.39 (3H, s), 1.30 (3H, s). Mass Spectrum (ESI) m/e=468 (M+1).

Workup

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

Sources & evidence

ORD record
ord-2d30d4a6ffb64dfd8134b53261370c5a
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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