2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → 7-Methoxy-3-(3-methoxymethoxy-pyridin-4-yl)-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

HRID 61906Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.I[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[O:23][CH2:24][O:25][CH3:26].CC(C)([O-])C.[Na+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[O:23][CH2:24][O:25][CH3:26])[C:9](=[O:15])[C:10]2([CH3:13])[CH3:14])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 924 mg), 4-iodo-3-methoxymethoxy-pyridine (1 g), sodium t-butoxide (906 mg), Pd2dba3 (173 mg) and S-Phos (185 mg), toluene (19 ml) was added, and the mixture was stirred and heated at 70° C. for 2 hrs under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate and filtered through Celite. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (610 mg, 47%).

Workup

filtrationfiltered through Celite
washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
concentrationconcentrated under reduced pressure
customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-b30c707f7e7b49c6a6252d91c6a15ff3
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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