Phenyl chloroformate → 3-[(1-Methylpyrazol-4-yl)methyl]-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea

HRID 2353690Notes

Reaction equation

HRID 2353690 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:12])([CH3:11])[O:9]2)=[CH:4][CH:3]=1.[C:17](=[O:20])(O)[O-].[Na+].C1(OC(Cl)=O)C=CC=CC=1.[CH3:32][N:33]1[CH:37]=[C:36]([CH2:38][NH2:39])[CH:35]=[N:34]1>C1COCC1>[CH3:32][N:33]1[CH:37]=[C:36]([CH2:38][NH:39][C:17](=[O:20])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([B:8]3[O:16][C:13]([CH3:15])([CH3:14])[C:10]([CH3:11])([CH3:12])[O:9]3)=[CH:4][CH:3]=2)[CH:35]=[N:34]1

Participants

6

Reactant 4

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 671225(1-methyl-1H-pyrazol-4-yl)methanamineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 593800143-[(1-Methylpyrazol-4-yl)methyl]-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Aminophenyl)boronic acid pinacol ester (200 mg) was dissolved in dry THF (5 mL) and sodium bicarbonate (116 mg) added followed by the dropwise addition of phenylchloroformate (0.115 mL). The mixture was stirred at RT for 1 hour. (1-Methylpyrazol-4-yl)methanamine (102 mg) was added and the reaction left to stir at RT for 2 h before being heated to 40° C. for 16 h. The mixture was concentrated in vacuo and the residue partitioned between DCM (25 mL) and water (25 mL). The organics were dried over magnesium sulphate, filtered and vacuumed to dryness. The material was chromatographed on silica, eluting with ethyl acetate, to give the desired material (232 mg) as a white solid.

Workup

  1. waitthe reaction left
  2. stirringto stir at RT for 2 h
  3. temperaturebefore being heated to 40° C. for 16 h
  4. concentrationThe mixture was concentrated in vacuo
  5. customthe residue partitioned between DCM (25 mL) and water (25 mL)
  6. dry with materialThe organics were dried over magnesium sulphate
  7. filtrationfiltered
  8. customThe material was chromatographed on silica
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4e016e7479cf4eb0b1787c32bdeaae03
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

Loading…