Nitrogen → HCID 50939992, compound

HRID 1618640Notes

Reaction equation

HRID 1618640 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([CH3:13])=[C:5]2[N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:21]=2)[C:16]([CH3:30])([CH3:29])[CH2:15]1.N#N.C(N(CC)CC)C>CO.[Pd]>[CH3:29][C:16]1([CH3:30])[C:17]2[C:22](=[CH:21][C:20]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:19][CH:18]=2)[N:14]([C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=3)[N:8]=[C:7]([CH3:12])[C:6]=2[CH3:13])[CH2:15]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 8471TriethylamineHCID 50940334HCID 50940334, compound

Product 1

HCID 50939992HCID 50939992, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(1-(6-chloro-2,3-dimethylquinolin-4-yl)-3,3-dimethylindolin-6-yl)morpholine (10 mg, 0.024 mmol) in MeOH (3 mL) was purged with N2. After the mixture was purged a catalytical amount of triethylamine and Pd/C (0.003 g, 0.002 mmol) were added. The resulting mixture was stirred at rt for 2 h under a hydrogen atmosphere. After this time the reaction mixture was filtered through a pad of Celite™ and the solvent was evaporated in vacuo to give 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-2,3-dimethylquinoline. 1H NMR (500 MHz, chloroform-d) δ ppm 8.06 (1H, br. s.), 7.73 (1H, d, J=8.3 Hz), 7.58 (1H, t, J=7.6 Hz), 7.33 (1H, t, J=7.6 Hz), 6.99 (1H, d, J=8.1 Hz), 6.23 (1H, d, J=7.1 Hz), 5.45 (1H, s), 3.63 (6H, m), 2.86 (4H, m), 1.43 (6H, m). Mass Spectrum (ESI) m/e=388 (M+1).

Workup

  1. additionwere added
  2. filtrationAfter this time the reaction mixture was filtered through a pad of Celite™
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4d70d623638f4ee4b0101e1c56d41005
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

Loading…