Triphenylphosphine → HCID 68285474, compound

HRID 1518741Notes

Reaction equation

HRID 1518741 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([S:12]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])=[O:13])=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:28][C:29]1[C:30](B2OC(C)(C)C(C)(C)O2)=[C:31]([C:34]([O:36][CH3:37])=[O:35])[S:32][CH:33]=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:16]([NH:15][S:12]([C:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:2]([C:30]2[C:29]([CH3:28])=[CH:33][S:32][C:31]=2[C:34]([O:36][CH3:37])=[O:35])=[CH:3][CH:4]=1)(=[O:14])=[O:13])([CH3:19])([CH3:18])[CH3:17]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 46702949HCID 46702949, compoundHCID 68286080HCID 68286080, compound

Product 1

HCID 68285474HCID 68285474, compoundYield 7.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

4-bromo-N-(tert-butyl)-5,6,7,8-tetrahydronaphthalene-1-sulfonamide (59b, 1.35 g, 3.90 mmol) and Potassium phosphate (0.75 g, 3.54 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, 1.0 g, 3.54 mmol) in a mixture of 20 ml THF and 4 ml water in a tube under a nitrogen atmosphere at room temperature (about 25° C.). A nitrogen gas was purged to this suspension for 15 minute at room temperature (about 25° C.). To the reaction mixture was then added triphenyl phospine (0.028 g, 0.10 mmol) and) Palladium (II) acetate (0.016 g, 0.07 mmol) at 25° C. and the tube was sealed. The reaction mixture was then stirred at about 75° C. for 20 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then filtered and the cake obtained was washed with ethyl acetate (2×30 ml). The combined filtrate was then concentrated under reduced pressure to obtain crude product, which was then purified by flash column chromatography using 30% ethyl acetate in hexanes as an eluent to obtain the title compound (0.11 g, 7.7%)

Workup

  1. customPrepared
  2. customA nitrogen gas was purged to this suspension for 15 minute at room temperature (about 25° C.)
  3. filtrationThe reaction mixture was then filtered
  4. customthe cake obtained
  5. washwas washed with ethyl acetate (2×30 ml)
  6. concentrationThe combined filtrate was then concentrated under reduced pressure
  7. customto obtain crude product, which
  8. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-f2ddd3d306304439bb3671d551dff008
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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