Cesium carbonate → HCID 50939991, compound

HRID 1618639Notes

Reaction equation

HRID 1618639 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]=[C:26]([Cl:29])[CH:27]=2)[N:22]=[C:21]([CH3:30])[C:20]=1[CH2:31][CH3:32].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]>[Cl:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]([CH3:30])[C:20]([CH2:31][CH3:32])=[C:19]2[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:6]=2)[C:2]([CH3:17])([CH3:1])[CH2:3]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 634091534,6-Dichloro-3-ethyl-2-methylquinolineHCID 672848583,3-Dimethyl-6-morpholinoindoline

Product 1

HCID 50939991HCID 50939991, 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 (0.033 g, 0.139 mmol), 4,6-dichloro-3-ethyl-2-methylquinoline (0.04 g, 0.167 mmol), cesium carbonate (0.091 g, 0.278 mmol), Pd2(dba)3 (0.013 g, 0.014 mmol) and (±) BINAP (0.013 g, 0.021 mmol) in 1,4-dioxane (1 mL). After purification by HPLC 6-chloro-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-3-ethyl-2-methylquinoline was obtained: 1H NMR (500 MHz, chloroform-d) δ ppm 8.40 (1H, d, J=9.0 Hz), 7.72 (1H, d, J=9.0 Hz), 7.68 (1H, s), 7.13 (1H, s), 6.57 (1H, d, J=8.1 Hz), 5.73 (1H, br. s.), 3.75 (4H, m), 2.97 (6H, br. s.), 1.44 (5H, d, J=16.4 Hz), 1.19 (6H, m), 0.80 (3H, d, J=15.4 Hz). Mass Spectrum (ESI) m/e=436 (M+1).

Workup

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

Sources & evidence

ORD record
ord-2be820cf248b406d9ceca9417fcb1a98
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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