Cesium carbonate → HCID 57826471, compound

HRID 1845568Notes

Reaction equation

HRID 1845568 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:16])[C:6]=1[C:7]1[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[S:10][CH:11]=1.[CH:17]1(B(O)O)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1>[CH:17]1([C:2]2[CH:3]=[N:4][N:5]([CH3:16])[C:6]=2[C:7]2[CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[S:10][CH:11]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2760897Cyclopropylboronic acidHCID 57826395methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 57826471HCID 57826471, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a 20 mL sealed tube reactor was added methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (505 mg, 1.68 mmol), cyclopropylboronic acid (447 mg, 5.20 mmol), Cesium Carbonate (1.90 g, 5.84 mmol) and PdCl2(dppf)-CH2Cl2Adduct (43.6 mg, 0.05 mmol) in Tetrahydrofuran (THF) (8.5 mL). The reaction was heated to 70° C. for 1.5 hours, cooled and partitioned between CHCl3 and H2O. The organic layer was dried with Na2SO4, adsorbed onto silica and purified via column chromatography (20-40% EtOAc/Hexane) affording the title compound (0.42 g, 1.60 mmol, 95%): LC-MS (ES) m/z=251 (M+H)+.

Workup

  1. customTo a 20 mL sealed tube reactor
  2. temperaturecooled
  3. custompartitioned between CHCl3 and H2O
  4. dry with materialThe organic layer was dried with Na2SO4
  5. custompurified via column chromatography (20-40% EtOAc/Hexane)

Sources & evidence

ORD record
ord-803f564d404e4b39bd464bd45f83d160
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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