Cesium carbonate → HCID 50940105, compound

HRID 1618615Notes

Reaction equation

HRID 1618615 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:18][C:19]1[CH:28]=[CH:27][C:26]2[N:25]=[C:24]3[CH2:29][CH2:30][CH2:31][C:23]3=[C:22](Cl)[C:21]=2[CH:20]=1.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>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].O1CCOCC1>[Cl:18][C:19]1[CH:28]=[CH:27][C:26]2[N:25]=[C:24]3[CH2:29][CH2:30][CH2:31][C:23]3=[C:22]([N:4]3[C:5]4[C:10](=[CH:9][CH:8]=[C:7]([N:11]5[CH2:16][CH2:15][O:14][CH2:13][CH2:12]5)[CH:6]=4)[C:2]([CH3:17])([CH3:1])[CH2:3]3)[C:21]=2[CH:20]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 24278824HCID 24278824, compoundHCID 672848583,3-Dimethyl-6-morpholinoindoline

Product 1

HCID 50940105HCID 50940105, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

Prepared according to procedure T using 4-(3,3-dimethylindolin-6-yl)morpholine (0.2 g, 0.86 mmol), 7,9-dichloro-2,3-dihydro-1H-cyclopenta[b]quinoline (0.41 g, 1.72 mmol), cesium carbonate (0.561 g, 1.72 mmol), Pd2(dba)3 (0.079 g, 0.086 mmol) and (±) BINAP (0.084 g, 0.129 mmol) were added 1,4-dioxane (2 mL). The resulting mixture was purged with Argon and subjected to microwave heating at 140° C. for 3 h. The crude residue was purified by HPLC to give 7-chloro-9-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2,3-dihydro-1H-cyclopenta[b]quinoline. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.07 (1H, d, J=2.0 Hz), 8.0 (1H, m), 7.94 (1H, dd, J=8.9, 2.1 Hz), 7.17 (1H, d, J=8.3 Hz), 6.64 (1H, dd, J=8.3, 2.0 Hz), 6.17 (1H, s), 4.33 (1H, d, J=9.3 Hz), 3.98 (1H, m), 3.66 (4H, dd, J=5.6, 3.9 Hz), 3.24 (2H, m), 2.97 (4H, dd, J=5.9, 3.7 Hz), 2.90 (1H, m), 2.61 (1H, m), 2.18 (2H, m), 1.30 (3H, s) 1.29 (3H, s). Mass Spectrum (ESI) m/e=434 (M+1).

Workup

  1. customPrepared
  2. customThe resulting mixture was purged with Argon
  3. customThe crude residue was purified by HPLC

Sources & evidence

ORD record
ord-a5c37b7ed09c410693559dcfd11c8e28
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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