Water → HCID 67810950, compound

HRID 2279893Notes

Reaction equation

HRID 2279893 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.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH2:26][C:27]1([CH2:30][O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)(=O)=O.O>CN(C=O)C>[CH2:32]([O:31][CH2:30][C:27]1([CH2:26][N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:29][CH2:28]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86697829{1-[(Benzyloxy)methyl]cyclopropyl}methyl methanesulfonate2×

Product 1

HCID 67810950HCID 67810950, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (8.62 g, 44.4 mmol) in DMF (12 mL) was treated with cesium carbonate (14.6 g, 44.4 mmol) and stirred at RT for 10 min. A solution of {1-[(benzyloxy)methyl]cyclopropyl}methyl methanesulfonate (Compound 63D, 12 g, 44.4 mmol) in DMF was added and heated to 70° C. for 24 hrs. The reaction mixture was cooled to RT, poured into water, extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated to give 12 g (73%) of required compound as a colorless gum which was used without further purification. 1H NMR (600 MHz, CDCl3) δ 7.78 (s, 1H), 7.68 (s, 1H), 7.25-7.34 (m, 5H), 4.48 (s, 2H), 4.15 (s, 2H), 3.16 (s, 2H), 1.33 (s, 12H), 0.71 (s, 2H), 0.56 (s, 2H).

Workup

  1. temperatureheated to 70° C. for 24 hrs
  2. temperatureThe reaction mixture was cooled to RT
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-63dff6083112412b9b9ff69934bbe560
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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