Triphenylphosphine → cis-3-Benzyl-6-(2,4-dichloro-phenyl)-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene

HRID 1714144Notes

Reaction equation

HRID 1714144 reaction equation
[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:11]([CH2:12][C:13]3[C:18]2=[CH:17][C:16](Br)=[CH:15][C:14]=3[CH3:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1B(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:11]([CH2:12][C:13]3[C:18]2=[CH:17][C:16]([C:27]2[CH:26]=[CH:25][C:24]([Cl:23])=[CH:29][C:28]=2[Cl:30])=[CH:15][C:14]=3[CH3:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 16117547cis-3-Benzyl-6-bromo-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoreneHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 16117676cis-3-Benzyl-6-(2,4-dichloro-phenyl)-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoreneYield 66.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound (85 mg, 0.20 mmol) was prepared by following the procedure of example 3 from cis-3-benzyl-6-bromo-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene (107 mg, 0.30 mmol), 2,4-dichlorophenylboronic acid (69 mg, 0.36 mmol), barium hydroxide octahydrate (142 mg, 0.45 mmol) and triphenylphosphine (7.9 mg, 0.03 mmol) and palladium(II) acetate (1.7 mg, 0.0075 mmol) in DMF (3.0 mL)/H2O (0.6 mL): MS (ES) 422.1 (M+H).

Sources & evidence

ORD record
ord-31187ca67d9f477f8037e49fefc3f836
Source dataset
uspto-grants-2010_09
Patent number
US07795436B2

Reaction notes

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