Water → HCID 58110270, compound

HRID 2068632Notes

Reaction equation

HRID 2068632 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 581103133-Iodo-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester

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-3d5c6870d68a423084b7b8b0c245def4
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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