Triphenylphosphine → HCID 68285856, compound

HRID 1053299Notes

Reaction equation

HRID 1053299 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[C:4]([CH3:16])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:25][C:26]1[C:27](B2OC(C)(C)C(C)(C)O2)=[C:28]([C:31]([O:33][CH3:34])=[O:32])[S:29][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:27]2[C:26]([CH3:25])=[CH:30][S:29][C:28]=2[C:31]([O:33][CH3:34])=[O:32])=[CH:3][C:4]=1[CH3:16])(=[O:10])=[O:9])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 46702949HCID 46702949, compoundHCID 68285661HCID 68285661, compound

Product 1

HCID 68285856HCID 68285856, compoundYield 43.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

4-bromo-N-(tert-butyl)-2-methylbenzenesulfonamide (Prepared according to the procedure reported in the literature, Tetrahedron, 2006, 62, 7902-7910, 1.43 g, 4.68 mmol) and Potassium phosphate (2.25 g, 10.63 mmol) were added to a stirred suspension of methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (Prepared according to the procedure reported in the literature, J. Org. Chem., 2010, 75, 3855-3858, 1.2 g, 4.25 mmol) in a mixture of 20 ml of THF and 4 ml of water in a tube under a nitrogen atmosphere at room temperature (25° C.). Nitrogen was purging was continued to this suspension for 15 minute at room temperature (25° C.). Triphenyl phospine (0.056 g, 0.21 mmol) and palladium (II) acetate (0.02 g, 0.08 mmol) were then added to it at 25° C. and the tube was sealed. Reaction mixture was stirred at 70° C. for 20 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then filtered and washed with ethyl acetate (2×30 ml). The organic layer was concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (0.7 g, 43.10%).

Workup

  1. customPrepared
  2. customNitrogen was purging
  3. custom(25° C.)
  4. customthe tube was sealed
  5. customReaction mixture
  6. filtrationThe reaction mixture was then filtered
  7. washwashed with ethyl acetate (2×30 ml)
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. customto obtain a crude product, which
  10. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-735537e1a3a34e4f98608cbd3f28d2cd
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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