Potassium Phosphate, Tribasic → HCID 70981716, compound

HRID 1409438Notes

Reaction equation

HRID 1409438 reaction equation
Br[C:2]1[N:3]([CH3:17])[CH:4]=[C:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:6]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][N:3]1[CH:4]=[C:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:6]=[C:2]1[C:30]1[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 70980972HCID 70980972, compound

Product 1

HCID 70981716HCID 70981716, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

Into a flask containing a solution of benzyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate (2 g, 6.77 mmol) in 1,2-dimethoxyethane (40 ml), potassium phosphate (2.3 g, 20.3 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.41 g, 6.77 mmol) were added at RT under argon atmosphere. The resulting mixture was degassed and purged with argon for 10 minutes. Then Pd(PPh3)4 (0.310 g, 0.2 mmol) was added to the reaction mixture and heated at 90° C. for 12 h. The reaction mixture was filtered through a celite bed and the filtrate was diluted with water and extracted with EtOAc. The organic layer was concentrated and purified by flash chromatography. Yield 1.1 g. 1H-NMR (400 MHz; CDCl3): δ 3.77 (s, 3H), 3.95 (s, 3H), 5.36 (s, 2H), 7.30-7.37 (m, 3H), 7.45 (d, 2H), 7.59 (s, 1H), 7.79 (s, 1H), 7.89 (s, 1H).

Workup

  1. additionwere added at RT under argon atmosphere
  2. customThe resulting mixture was degassed
  3. custompurged with argon for 10 minutes
  4. filtrationThe reaction mixture was filtered through a celite bed
  5. additionthe filtrate was diluted with water
  6. extractionextracted with EtOAc
  7. concentrationThe organic layer was concentrated
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b375d6a9973b43fe9d85241114e53f4e
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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