Potassium Carbonate → HCID 69429842, compound

HRID 1269462Notes

Reaction equation

HRID 1269462 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH2:17][C:18]([NH:20][CH:21]2[CH2:30][CH2:29][CH2:28][C:27]3[CH:26]=[C:25](OS(C(F)(F)F)(=O)=O)[CH:24]=[CH:23][C:22]2=3)=[O:19])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[C:41]([O:45][C:46](=[O:51])[NH:47][CH2:48][CH:49]=[CH2:50])([CH3:44])([CH3:43])[CH3:42].C([O-])([O-])=O.[K+].[K+]>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:41]([O:45][C:46](=[O:51])[NH:47][CH2:48][C:49]([C:25]1[CH:24]=[CH:23][C:22]2[CH:21]([NH:20][C:18](=[O:19])[CH2:17][CH:13]3[CH2:14][CH2:15][CH2:16][N:12]3[S:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:39])([F:40])[F:1])[CH:4]=3)(=[O:11])=[O:10])[CH2:30][CH2:29][CH2:28][C:27]=2[CH:26]=1)=[CH2:50])([CH3:44])([CH3:43])[CH3:42]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamateHCID 86601067HCID 86601067, compound

Product 1

HCID 69429842HCID 69429842, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of trifluoro-methanesulfonic acid 5-{2-[1-(3-trifluoromethyl-benzenesulfonyl)-pyrrolidin-2-yl]-acetylamino}-5,6,7,8-tetrahydro-naphthalen-2-yl ester (150 mg, 0.244 mmol, 1.0 eq), allyl carbamic acid tert-butyl ester (230 mg, 1.47 mmol, 6.0 eq), palladium acetate (Strem Chemicals, 3.3 mg, 0.015 mmol, 0.06 eq), DPPF (Aldrich, 36 mg, 0.064 mmol, 0.26 eq) and K2CO3 (Aldrich, 51 mg, 0.37 mmol, 1.5 eq) in CH3CN (2 mL) was flushed with N2 for 10 min. The reaction was heated to 80° C. and stirred at 80° C. under N2 for 20 h. The reaction was quenched with H2O (60 mL), extracted with CH2Cl2 (60 mL×3). The extract phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated in vacuo. Flash column chromatography (silica gel, 0–4% MeOH—CH2Cl2) afforded the title compound as a colorless thin film. MS (ESI, pos. ion) m/z: 622 (M+1).

Workup

  1. customwas flushed with N2 for 10 min
  2. customThe reaction was quenched with H2O (60 mL)
  3. extractionextracted with CH2Cl2 (60 mL×3)
  4. washThe extract phase was washed with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-377471398b2245479e96847820985226
Source dataset
uspto-grants-2007_04
Patent number
US07199244B2

Reaction notes

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