Cesium carbonate → HCID 59402346, compound

HRID 2090416Notes

Reaction equation

HRID 2090416 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[CH2:15](Br)[CH:16]1[O:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[O:20]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:15][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 59402346HCID 59402346, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (50 mg, 0.2 mmol), tetrahydrofurfuryl bromide (51 mg, 0.31 mmol, Alfa Aesar, Cat. No. A15192), and cesium carbonate (250 mg, 0.77 mmol) in acetonitrile (1 mL) was stirred at 90° C. overnight. After cooling, it was diluted with ethyl acetate. The organic solution was washed with water and brine, and dried over Na2SO4. After filtration the filtrate was concentrated to yield 51 mg of the product.

Workup

  1. temperatureAfter cooling
  2. washThe organic solution was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration the filtrate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-07d9dcc8f9ff464a8b5aefb3224679bd
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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