Triethylamine → HCID 67285103, compound

HRID 1618606Notes

Reaction equation

HRID 1618606 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:27]2[C:22](=[CH:23][CH:24]=[C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:26]=2)[C:16]2([CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:15]1.C(N(CC)CC)C>CO.CCOC(C)=O.[Pd]>[CH3:12][C:7]1[C:6]([CH3:13])=[C:5]([N:14]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([N:28]4[CH2:29][CH2:30][O:31][CH2:32][CH2:33]4)[CH:26]=3)[C:16]3([CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[CH2:15]2)[C:4]2[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=2)[N:8]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 50939474HCID 50939474, compound

Product 1

HCID 67285103HCID 67285103, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 1-(6-chloro-2,3-dimethylquinolin-4-yl)-6-morpholino-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (0.027 g, 0.058 mmol), triethylamine (0.008 mL, 0.058 mmol), and 10% Pd/C (0.02 g, 0.0188 mmol) in MeOH-EtOAc (2:1, 3 mL) was stirred under hydrogen at rt. After 3 h, the mixture was filtered through a Celite™ pad and the pad was washed with MeOH and EtOAc to give a tan solid. The tan solid was purified by column chromatography on a silica gel column using 0 to 100% gradient of EtOAc in hexane as eluent to give 1-(2,3-dimethyl-4-quinolinyl)-6-(4-morpholinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran] as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 7.97 (1H, d, J=8.3 Hz), 7.71 (1H, d, J=8.1 Hz), 7.62-7.68 (1H, m), 7.42-7.49 (1H, m), 7.08 (1H, d, J=8.3 Hz), 6.23 (1H, dd, J=8.2, 2.1 Hz), 5.41 (1H, d, J=2.2 Hz), 3.77-3.96 (4H, m), 3.52-3.59 (4H, m), 3.41-3.51 (2H, m), 2.81 (4H, dd, J=5.4, 2.9 Hz), 2.68 (3H, s), 2.22 (3H, s), 1.91-2.03 (2H, m), 1.78-1.85 (1H, m), 1.65-1.72 (1H, m); Mass Spectrum (ESI) m/e=430.2 (M+1).

Workup

  1. filtrationthe mixture was filtered through a Celite™ pad
  2. washthe pad was washed with MeOH and EtOAc
  3. customto give a tan solid
  4. customThe tan solid was purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-ce3ee3c1d49140e2a8dbfe3cf3e4a7f0
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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