Cesium carbonate → HCID 67468254, compound

HRID 2171163Notes

Reaction equation

HRID 2171163 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH:11]([F:13])[F:12])[C:3]=1[O:14][CH2:15][O:16][CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:32]2[CH:40]=[CH:39][CH:38]=[C:37]3[C:33]=2[CH2:34][CH2:35][C:36]3=[O:41])O1>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:12][CH:11]([F:13])[O:10][C:4]1[C:3]([O:14][CH2:15][O:16][CH3:17])=[C:2]([C:32]2[CH:40]=[CH:39][CH:38]=[C:37]3[C:33]=2[CH2:34][CH2:35][C:36]3=[O:41])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 220320882,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-1-oneHCID 67465272HCID 67465272, compound

Product 1

HCID 67468254HCID 67468254, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1-bromo-3-(difluoromethoxy)-4-methoxy-2-(methoxymethoxy)benzene (3 g, 9.58 mmol) in dimethylformamide (50 mL) was purged with argon for 1 h, to this cesium carbonate (9.34 g, 28.74 mmol), tetrakis(triphenylphosphine) palladium (0) (1.1 g, 0.958 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (2.96 g, 11.49 mmol) were added and the resultant reaction mixture was heated to 80° C. for 4 h. The reaction mixture was cooled to RT and filtered and the filtrate was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-20% ethyl acetate in pet ether) afforded 4-(3-(Difluoromethoxy)-4-methoxy-2-(methoxymethoxy)phenyl)-2,3-dihydro-1H-inden-1-one as a solid (1.8 g, 51.6%).

Workup

  1. additionwere added
  2. customthe resultant reaction mixture
  3. temperatureThe reaction mixture was cooled to RT
  4. filtrationfiltered
  5. additionthe filtrate was diluted with water
  6. extractionextracted with ethyl acetate (3×)
  7. washThe combined ethyl acetate layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customPurification by column chromatography (silica gel, 0-20% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-e159e49cc45d4a5d840cf250215b7476
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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