Water → 3-(3-Benzyl-8-trifluoromethyl-cinnolin-4-yl)-phenol

HRID 643341Notes

Reaction equation

HRID 643341 reaction equation
[CH2:1]([C:8]1[N:9]=[N:10][C:11]2[C:16]([C:17]=1Br)=[CH:15][CH:14]=[CH:13][C:12]=2[C:19]([F:22])([F:21])[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.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>[CH2:1]([C:8]1[N:9]=[N:10][C:11]2[C:16]([C:17]=1[C:28]1[CH:29]=[C:24]([OH:23])[CH:25]=[CH:26][CH:27]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:19]([F:22])([F:21])[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 685814793-Benzyl-4-bromo-8-trifluoromethyl-cinnoline

Product 1

HCID 118543123-(3-Benzyl-8-trifluoromethyl-cinnolin-4-yl)-phenolYield 74.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-benzyl-4-bromo-8-trifluoromethyl-cinnoline (1.7 g, 4.6 mmol) and 3-hydroxyphenylboronic acid (0.84 g, 6.0 mmol) and Pd(PPh3)4 (300 mg) and K3PO4 (3.0 g) in dioxane (50 ml) was heated to reflux. After 6 hr, the reaction was cooled and poured into water and extracted with EtOAc. The organic layer was concentrated and the product purified by colum chromatography (eluent 10% EtOAc/Hexane) to give a solid 1.3 g. MS (ES) m/z 381.1.

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated
  4. customthe product purified by colum chromatography (eluent 10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-e1ef815d526b414999e1425f8347b30c
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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