Tetrafluoroboric acid → HCID 89545229, compound

HRID 1507539Notes

Reaction equation

HRID 1507539 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.[CH:11]1(B(O)O)[CH2:13][CH2:12]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[H+].[B-](F)(F)(F)F>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:11]1([C:2]2[CH:3]=[CH:4][C:5]3[S:9][CH:8]=[N:7][C:6]=3[CH:10]=2)[CH2:13][CH2:12]1

Participants

9

Reactant 5

HCID 28118Tetrafluoroboric acidHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 36101555-Bromobenzothiazole

Product 1

HCID 89545229HCID 89545229, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Following the same procedure in step 1 of Example 344 using 5-bromo-1,3-benzothiazole (500 mg, 2.34 mmol, 1.00 equiv), cyclopropylboronic acid (300 mg, 3.49 mmol, 1.50 equiv), potassium phosphate (2.2 g, 10.36 mmol, 4.50 equiv), palladium acetate (51.6 mg, 0.10 equiv), and PCy3.HBF4 (0.17 g, 0.20 equiv) in a mixture of toluene (12 mL) and water (1.2 mL). The crude product was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (10:1-5:1) to provide the title compound as a purple oil. MS m/z [M+H]+ (ESI): 176.

Workup

  1. customThe crude product was purified by flash chromatography on silica gel
  2. washeluting with petroleum ether/ethyl acetate (10:1-5:1)

Sources & evidence

ORD record
ord-727c5d0497164b88abc369341db6ab3d
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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