Sodium Carbonate → 6-(2-Methylpyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63634Notes

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.[CH3:23][C:24]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[CH:26][N:25]=1.C([O-])([O-])=O.[Na+].[Na+].[Li]Cl.O>CCO.O.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:23][C:24]1[CH:29]=[C:28]([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)[CH:27]=[CH:26][N:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl 4-methylbenzene-1-sulfonate (1.3 g, 4.4 mmol), 2-methylpyridine-4-boronic acid pinacol ester (800 mg, 3.7 mmol), Na2CO3 (773 mg, 7.3 mmol) and LiCl.H2O (442 mg, 7.3 mmol) in EtOH/H2O/toluene (4.4 mL/2.3 mL/20.0 mL) was added Pd(PPh3)4 (211 mg, 0.2 mmol) at rt under N2. The reaction was stirred at 100° C. overnight. The reaction was filtered and concentrated. Purification by silica gel chromatography (PE:EtOAc=1:1) gave 865 mg (quantitative) of the title compound as a yellow solid. [M+H] Calc'd for C16H15NO, 238. Found, 238.

Workup

filtrationThe reaction was filtered
concentrationconcentrated
customPurification by silica gel chromatography (PE:EtOAc=1:1)

Sources & evidence

ORD record: ord-73013d00dc0244d89fe14fca78fe4c72
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447046B2

Reaction notes

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