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Sodium Carbonate → 2-m-Tolyl-6-(trifluoromethyl)nicotinonitrile

HRID 1428732
Notes
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Reaction equation

HRID 1428732 reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:14]1([CH3:23])[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.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:14]1([CH3:23])[CH:19]=[CH:18][CH:17]=[C:16]([C:2]2[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 27784132-Chloro-6-(trifluoromethyl)nicotinonitrileHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 866802152-m-Tolyl-6-(trifluoromethyl)nicotinonitrileYield 49%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-6-(trifluoromethyl)nicotinonitrile (3 g, 14.56 mmol) was dissolved in toluene (70 mL) and ethanol (14 mL). m-tolylboronic acid (2.969 g, 21.814 mmol), aqueous sodium carbonate solution (2 M, 14 mL) and Pd(PPh3)4 (1.684 g, 1.456 mmol) were added. The mixture was flushed with nitrogen and stirred under microwave conditions (7 bar) at 100° C. for 2 h. The concentrated reaction mixture was cooled, diluted with ethyl acetate (200 mL), passed through celite (cyclohexane/ethyl acetate 9:1, 2×1 L) and concentrated in vacuo to afford 2-m-tolyl-6-(trifluoromethyl)nicotinonitrile (1.87 g, 49%).

Workup

  1. customThe mixture was flushed with nitrogen
  2. customThe concentrated reaction mixture
  3. temperaturewas cooled
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f30511677c749ccbacfa832fd2b2618
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937092B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes