Cesium carbonate → HCID 118510791, compound

HRID 1053792Notes

Reaction equation

HRID 1053792 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[CH:11]([B-](F)(F)F)=[CH2:12].[K+].C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH4+].[Cl-]>C1COCC1.Cl[Pd]Cl.O>[CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1)=[CH2:12]

Participants

9

Reactant 5

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 127444006-Bromo-benzo[b]thiopheneHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 118510791HCID 118510791, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 6-bromobenzo[b]thiophene (217 mg, 1.02 mmol), potassium vinyltrifluoroborate (137 mg, 1.02 mmol), Cs2CO3 (983 mg, 3.02 mmol), Ph3P (17 mg, 0.066 mmol) and PdCl2 (5 mg, 0.028 mol) in THF (1.8 mL)/H2O (0.2 mL) was heated at 85° C. After overhight stirring, H2O (5 mL) and saturated NH4Cl solution (50 mL) were added and the resulting mixture was extracted with CH2Cl2 (3×25 mL). The combined organic solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (67 mg, 41%).

Workup

  1. extractionthe resulting mixture was extracted with CH2Cl2 (3×25 mL)
  2. dry with materialThe combined organic solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-07d8b151f14b45c3844ce9c7d2c09582
Source dataset
uspto-grants-2016_07
Patent number
US09394273B2

Reaction notes

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