2-Propanethiol → 2'-Fluoro-2-isopropylsulfanyl-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

HRID 1662492Notes

Reaction equation

HRID 1662492 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1I.C(N(C(C)C)C(C)C)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.[CH3:72][CH:73]([SH:75])[CH3:74]>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>[CH3:19][O:18][C:16]([C:13]1[CH:14]=[CH:15][C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[C:11]([S:75][CH:73]([CH3:74])[CH3:72])[CH:12]=1)=[O:17]

Participants

7

Reactant 4

HCID 63642-PropanethiolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57705628Methyl 2'-fluoro-2-iodo-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 574676382'-Fluoro-2-isopropylsulfanyl-5'-methoxy-biphenyl-4-carboxylic acid methyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A tube was charged with 66.15D (213 mg, 552 μmol), N-ethyl-N-isopropylpropan-2-amine (143 mg, 1103 μmol) and toluene, evacuated and back-filled with nitrogen three times. Pd2(dba)3, 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (31.9 mg, 55.2 μmol) and propane-2-thiol (63.0 mg, 827 μmol) were added to the mixture and then the mixture was degassed three times. The suspension was refluxed overnight, filtered, and concentrated to give a residue which was purified by silica gel chromatography to give 69.24A as a pale yellow solid (164 mg, 89%). MS ESI m/e: 335.2 (M+1)+.

Workup

  1. customevacuated
  2. additionback-filled with nitrogen three times
  3. customthe mixture was degassed three times
  4. temperatureThe suspension was refluxed overnight
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-8019040c0c144d1d9586131756126d84
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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