Cesium carbonate → HCID 86668874, compound

HRID 242889Notes

Reaction equation

HRID 242889 reaction equation
Br[C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[S:5][C:6]=1[CH:7]=[O:8].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]1([CH3:13])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[S:5][C:6]=1[CH:7]=[O:8]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27332672-Methylphenyl boronic acidHCID 125060143-Bromo-1-benzothiophene-2-carbaldehyde

Product 1

HCID 86668874HCID 86668874, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-bromobenzo[b]thiophene-2-carbaldehyde (500 mg, 2.07 mmol), 2-methylphenylboronic acid (394 mg, 2.90 mmol), Pd(PPh3)4 (243 mg, 0.21 mmol), Cs2CO3 (2.02 g, 6.21 mmol) in dioxane (12 mL) and water (4 mL) was degassed with a stream of nitrogen then heated at 130° C. in a sealed tube using microwave irradiation for 45 min. The reaction mixture was extracted with EtOAc, and the organic fraction washed with water, followed by brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-70% DCM in cyclohexane) affording the title compound (quantitative yield). LCMS (Method C): RT 4.16 min

Workup

  1. customwas degassed with a stream of nitrogen
  2. custommicrowave irradiation for 45 min
  3. extractionThe reaction mixture was extracted with EtOAc
  4. washthe organic fraction washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-70% DCM in cyclohexane)

Sources & evidence

ORD record
ord-af0c99e1ae0946f28f54f3d293a32d10
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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