Cesium carbonate → HCID 50940106, compound

HRID 1618616Notes

Reaction equation

HRID 1618616 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:32]=[C:31]2[C:22]([N:23]=[C:24]3[C:29](=[C:30]2Cl)[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:21][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>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:18][C:19]1[CH:32]=[C:31]2[C:22]([N:23]=[C:24]3[C:29](=[C:30]2[N:4]2[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]2)[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 10514940HCID 10514940, compoundHCID 672848583,3-Dimethyl-6-morpholinoindoline

Product 1

HCID 50940106HCID 50940106, 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 (0.2 g, 0.86 mmol), 7,9-dichloro-1,2,3,4-tetrahydroacridine (0.434 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) in 1,4-dioxane (2 mL). 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)-1,2,3,4-tetrahydroacridine. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.04 (1H, d, J=9.5 Hz), 7.85 (2H, m), 7.14 (1H, d, J=8.3 Hz), 6.47 (1H, d, J=8.3 Hz), 5.84 (1H, s), 3.90 (2H, m), 3.60 (4H, m), 3.17 (2H, t, J=6.4 Hz), 2.89 (4H, m), 2.59 (2H, m), 1.79 (4H, m) 1.41 (3H, s), 1.37 (3H, s). Mass Spectrum (ESI) m/e=449 (M+1).

Workup

  1. customPrepared
  2. customThe crude residue was purified by HPLC

Sources & evidence

ORD record
ord-1c85c1904dd04ad0858cae48041562f1
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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