Cesium carbonate → HCID 50940456, compound

HRID 1618582Notes

Reaction equation

HRID 1618582 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](=[C:24]([Cl:30])[CH:25]=[C:26]([CH3:29])[CH:27]=2)[N:22]=[C:21]([CH3:31])[C:20]=1[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>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:30][C:24]1[CH:25]=[C:26]([CH3:29])[CH:27]=[C:28]2[C:23]=1[N:22]=[C:21]([CH3:31])[C:20]([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 63409230HCID 63409230, compoundHCID 672848583,3-Dimethyl-6-morpholinoindoline

Product 1

HCID 50940456HCID 50940456, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

A dry, microwave vial containing 4-(3,3-dimethylindolin-6-yl)morpholine (150.7 mg, 0.65 mmol), 4,8-dichloro-2,3,6-trimethylquinoline (233.8 mg, 0.97 mmol), cesium carbonate (317.0 mg, 0.97 mmol), Pd2(dba)3 (119 mg, 0.13 mmol), rac-BINAP (81.6 mg, 0.13 mmol), and dry 1,4-dioxane (2.2 mL) was evacuated and backfilled with argon. The mixture was heated in the microwave at 140° C. After 2 h, the reaction was filtered then concentrated under reduced pressure. The residue was purified on silica gel (0-100% EtOAc in hexane) to afford an impure film that was triturated with isopropanol to afford 8-chloro-4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2,3,6-trimethylquinoline. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.71 (1H, d, J=1.5 Hz), 7.52 (1H, s), 7.03 (1H, d, J=8.1 Hz), 6.23 (1H, s), 5.44 (1H, s), 3.72 (1H, d, J=9.0 Hz), 3.59 (4H, m), 3.53 (1H, s), 3.33 (2H, s), 2.83 (4H, s), 2.69 (3H, s), 2.40 (3H, s), 2.18 (3H, s), 1.44 (3H, s), 1.39 (3H, s). Mass Spectrum (ESI) m/e=436.1 (M+1).

Workup

  1. customwas evacuated
  2. filtrationthe reaction was filtered
  3. concentrationthen concentrated under reduced pressure
  4. customThe residue was purified on silica gel (0-100% EtOAc in hexane)
  5. customto afford an impure film that
  6. customwas triturated with isopropanol

Sources & evidence

ORD record
ord-108613e81a45419294c5370ee6709960
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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