Cesium carbonate → 6-(1,2,3,4-Tetrahydroquinolin-1-yl)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63615Notes

Reaction equation

HRID 63615 reaction equation
CC1C=CC(S(O[C:12]2[CH:21]=[CH:20][C:19]3[C:18](=[O:22])[CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=2)(=O)=O)=CC=1.[NH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH2:24]1.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.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:23]1([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18](=[O:22])[CH2:17][CH2:16][CH2:15]3)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 694601,2,3,4-TetrahydroquinolineHCID 634876Binap, (A+-)-HCID 1185977705-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 1185979266-(1,2,3,4-Tetrahydroquinolin-1-yl)-1,2,3,4-tetrahydronaphthalen-1-oneYield 76.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl 4-methylbenzene-1-sulfonate (1.0 g, 3.4 mmol) in THF (20 mL) was added 1,2,3,4-tetrahydroquinoline (0.55 g, 4.1 mmol), Pd(OAc)2 (92 mg, 0.41 mmol), BINAP (383 mg, 0.61 mmol) and Cs2CO3 (1.7 g, 5.1 mmol). The mixture was heated to reflux under nitrogen overnight. The mixture was filtered and concentrated, and the residue was purified by silica gel chromatography (10% EtOAc/hexanes) to give 0.72 g (76%) of the title compound as a brown oil. 1H NMR (400 MHz, CDCl3): δ 7.94 (d, J=8.4 Hz, 1H), 7.18-7.04 (m, 4H), 6.97 (d, J=2.4 Hz, 1H), 6.90 (dt, J=7.6 Hz, 1.2 Hz, 1H), 3.69 (t, J=6.0 Hz, 2H), 2.87 (t, J=6.0 Hz, 2H), 2.77 (t, J=6.4 Hz, 2H), 2.61 (t, J=6.4 Hz, 2H), 2.14-2.08 (m, 2H), 2.05-1.98 (m, 2H). [M+H] calc'd for C19H19NO, 278. found 278.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen overnight
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0f11fabc93c54e9eb6366bdc07056abc
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Reaction notes

Loading…