Triphenylphosphine → HCID 69097659, compound

HRID 1626934Notes

Reaction equation

HRID 1626934 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:12])[CH:5]=[C:4]([C@@H:13]([NH:15][C:16](=[O:32])[O:17][CH2:18][CH:19]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH3:14])[N:3]=1.[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([CH:33]=[CH2:34])=[N:3][C:4]([C@@H:13]([NH:15][C:16](=[O:32])[O:17][CH2:18][CH:19]1[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[C:31]1=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:14])=[CH:5]2

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 86665027(S)-(9H-fluoren-9-yl)methyl 1-(1,8-dichloroisoquinolin-3-yl)ethylcarbamate

Product 1

HCID 69097659HCID 69097659, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-(9H-fluoren-9-yl)methyl-1-(1,8-dichloroisoquinoline-3-yl)ethylcarbamate (346) (36 g, 77.7 mmol, 1.0 eq) in THF (300 mL) under argon, tributyl(vinyl)stannane (27 g, 85.5 mmol, 1.1 eq), Pd(OAc)2 (5.23 g, 23.3 mmol, 0.3 eq) and PPh3 (12.2 g, 46.6 mmol, 0.6 eq) were added, and the resulting mixture was stirred at reflux for 16 h. The mixture was allowed to cool to RT and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (2-30% ethyl acetate-petroleum ether) to afford (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-vinylisoquinolin-3-yl)ethylcarbamate (347).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (2-30% ethyl acetate-petroleum ether)

Sources & evidence

ORD record
ord-97a0883865cf42edaaccfc634d6a1ee6
Source dataset
uspto-grants-2014_07
Patent number
US08785470B2

Reaction notes

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