Water → HCID 24873257, compound

HRID 2106290Notes

Reaction equation

HRID 2106290 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:11](=[C:12]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(B(O)O)C=CC=CC=1.O>O1CCOCC1>[C:18]1([N:13]2[C:12]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[C:11]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9][CH2:10]3)=[N:14]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic Acid2×HCID 67269434HCID 67269434, compound

Product 1

HCID 24873257HCID 24873257, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2,3-Diphenyl-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester. To a solution of the above compound (0.28 g) in 5 mL of 1,4-dioxane was added 0.29 g of K3PO4, 104.3 mg of phenylboronic acid and 43.0 mg of PdCl2dppf. The mixture was heated at 80° C. for 3 h. More phenylboronic acid (0.10 g) and PdCl2dppf (26 mg) were added and the temperature was increased to 100° C. After an additional 12 h, the mixture was poured into water (100 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layers were filtered through diatomaceous earth and the filtrate was concentrated in vacuo. Chromatography on SiO2 (0 to 20% EtOAc/hexanes) afforded 158.8 mg of the desired compound. MS (ESI): exact mass calculated for C24H27N3O2, 389.21; found, m/z 390.2 [M+H]+.

Workup

  1. temperaturethe temperature was increased to 100° C
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. filtrationThe combined organic layers were filtered through diatomaceous earth
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fb9989aae6da493d8aac57629ecea166
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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