Toluene → HCID 21865165, compound

HRID 857655Notes

Reaction equation

HRID 857655 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)[CH:3]=1.C1(C)C=CC=CC=1.[F:26][C:27]([F:39])([F:38])[O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>O.[OH-].[Na+].CCO>[F:26][C:27]([F:38])([F:39])[O:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]3[CH:18]=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[N:16]4)=[CH:11][CH:10]=3)[CH:3]=2)=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 21865161HCID 21865161, compound

Product 1

HCID 21865165HCID 21865165, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
140 °C

Procedure

To a 5-mL, microwave vial containing 7-(6-chloro-pyrimidin-4-yloxy)-quinoline, (Example 102(a)), (0.30 g, 1.2 mmol) and 1:1 toluene:EtOH (2.5 mL) was added 4-trifluoromethoxyphenylboronic acid (0.30 g, 1.9 mmol, Aldrich), 2 N potassium carbonate (2.5 mL), and palladium(0)-tetrakis-triphenylphosphine (0.070 g, 0.060 mmol, Strem Chemical). The reaction mixture was heated at 140° C. for 10 min in a microwave synthesizer, allowed to cool to room temperature and diluted with water (5 mL) and 1 N sodium hydroxide (50 mL). The product was extracted with dichloromethane (2×100 mL), dried over sodium sulfate, and concentrated in vacuum. The crude material was purified by silica gel chromatography (gradient: 1–1.7% 2 N ammonia in methanol/dichloromethane) to obtain the title compound as a white solid. Mp: 67–168° C. MS (ESI, pos. ion.) m/z: 384 (M+1).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe product was extracted with dichloromethane (2×100 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuum
  5. customThe crude material was purified by silica gel chromatography (gradient: 1–1.7% 2 N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-15a77849b81f46488982a6d56456d239
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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