Water → HCID 58110270, compound

HRID 1914567Notes

Reaction equation

HRID 1914567 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[S:7][CH:6]=1)=[O:4].O.C(OC([N:27]1[C:31]([CH3:32])=[CH:30][C:29](I)=[N:28]1)=O)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.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.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:29]2[CH:30]=[C:31]([CH3:32])[NH:27][N:28]=2)[S:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 53399678Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carboxylateHCID 58110313HCID 58110313, compound

Product 1

HCID 58110270HCID 58110270, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
140 °C

Procedure

5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-3-carboxylic acid methyl ester (0.10 g, 0.37 mmol) was dissolved in DME (3 mL), IMS 1 mL) and water (0.5 mL) and 3-iodo-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.125 g, 0.41 mmol) was added followed by caesium carbonate (0.18 g, 0.56 mmol). The mixture was degassed and purged with nitrogen then palladium tetrakis(triphenylphosphine) (0.043 g, 0.04 mmol) was added. The reaction mixture was purged with nitrogen then heated by microwave irradiation to 140° C. for 20 minutes. The mixture was diluted with water then extracted with DCM (×3) then the organic solution was dried over sodium sulfate, filtered and the solvent evaporated. The residue was purified by chromatography on a 5 g silica II cartridge, eluting with 10-33% ethyl acetate in cyclohexane to give the title compound as a tan semi-solid material (0.052 g). LCMS m/z 223.02 [M+H]+ R.T.=2.93 min (Analytical Method 6).

Workup

  1. customThe mixture was degassed
  2. custompurged with nitrogen
  3. customThe reaction mixture was purged with nitrogen
  4. additionThe mixture was diluted with water
  5. extractionthen extracted with DCM (×3)
  6. dry with materialthe organic solution was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customThe residue was purified by chromatography on a 5 g silica II cartridge
  10. washeluting with 10-33% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-1b0e341c101c459eb971db48af670b07
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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