Sodium Carbonate → HCID 21921862, compound

HRID 1245061Notes

Reaction equation

HRID 1245061 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([NH:10][C:11]2[N:12]=[C:13](Br)[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:9])=[CH:3][CH:2]=1.[F:28][C:29]([F:40])([F:39])[C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1.C([O-])([O-])=O.[Na+].[Na+]>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>[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([NH:10][C:11]2[N:12]=[C:13]([C:33]3[CH:32]=[CH:31][C:30]([C:29]([F:40])([F:39])[F:28])=[CH:35][CH:34]=3)[C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:9])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 21921391HCID 21921391, compound

Product 1

HCID 21921862HCID 21921862, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of Example 14 (0.1 g, 0.24 mmol), 3-trifluoromethylphenylboronic acid (0.14 g, 0.72 mmol), Pd(PPh3)4 (0.028 g, 0.024 mmol) and 2N Na2CO3 solution (0.1 ml) in DME was heated at 75° C. for 12 h under nitrogen. The reaction mixture was cooled, and the solvent was evaporated. The resulting residue was purified by flash column chromatography (SiO2, 10% ethyl acetate in hexane) to provide the title compound (0.1 g, 87%) as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was evaporated
  3. customThe resulting residue was purified by flash column chromatography (SiO2, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-942a9ac9442e454186b2412e01b61ac9
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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