Triphenylphosphine → HCID 16117541, compound

HRID 1714137Notes

Reaction equation

HRID 1714137 reaction equation
[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:11]([C:12](=[O:22])[C:13]3[C:18]2=[CH:17][CH:16]=[CH:15][C:14]=3Br)[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]([C:12](=[O:22])[C:13]3[C:18]2=[CH:17][CH:16]=[CH:15][C:14]=3[C:27]2[CH:26]=[CH:25][C:24]([Cl:23])=[CH:29][C:28]=2[Cl:30])[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 16117814HCID 16117814, compoundHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 16117541HCID 16117541, compoundYield 41.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound (90 mg, 0.21 mmol) was prepared by following the procedure of example 3 from cis-3-benzyl-8-bromo-1,2,3,4,4a,9a-hexahydro-3-aza-fluoren-9-one (172 mg, 0.51 mmol), 2,4-dichlorophenylboronic acid (153 mg, 0.80 mmol), barium hydroxide octahydrate (317 mg, 1.0 mmol) and triphenylphosphine (18 mg, 0.067 mmol) and palladium(II) acetate (3.8 mg, 0.017 mmol) in DMF (6.0 mL)/H2O (1.2 mL): MS (ES) 422.1 (M+H).

Sources & evidence

ORD record
ord-62c7f78015bd40868a8f50e6225947b2
Source dataset
uspto-grants-2010_09
Patent number
US07795436B2

Reaction notes

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