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

HRID 594765Notes

Reaction equation

HRID 594765 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-98b3822de8b9403aba4bc7bfecda9b95
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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