Potassium Phosphate, Tribasic → HCID 59752554, compound

HRID 2106214Notes

Reaction equation

HRID 2106214 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:13]=[C:12]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].FC(F)(F)C1C=CC(B(O)O)=CC=1>C1COCC1>[CH2:18]([N:14]1[C:15]2[CH2:16][CH2:17][NH:8][CH2:9][CH2:10][C:11]=2[C:12]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=2)=[N:13]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 67269000HCID 67269000, compound

Product 1

HCID 59752554HCID 59752554, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-3-(4-trifluoromethyl-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. To a solution of the compound from step C (0.17 g) in 5 mL of THF was added 0.12 g of K3PO4, 0.08 g of 4-trifluoromethylphenylboronic acid and 0.03 g of PdCl2dppf. The mixture was heated at reflux for 12 h. The mixture was cooled, filtered through diatomaceous earth, and concentrated in vacuo. Chromatography on SiO2 (5 to 40% EtOAc/hexanes) afforded 0.05 g of the desired compound. TLC (SiO2, 25% EtOAc/hexanes): Rf=0.49.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through diatomaceous earth
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e4a63fbd465424e85f20363f4e01d6f
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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