Potassium Carbonate → HCID 23159793, compound

HRID 1011438Notes

Reaction equation

HRID 1011438 reaction equation
C([C:3]1[N:10]=[C:9](Br)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6])C.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][N:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 23159768HCID 23159768, compound

Product 1

HCID 23159793HCID 23159793, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 6-bromonicotinonitrile (1.81 g, 10 mmol) described in the Journal of Organic Chemistry 2001, 66, 1500-1502, 2-methoxyphenylboronic acid (1.22 g, 10 mmol), Pd(PPh3)4 (5% mol), K2CO3 (5 g) in DMF/water (3/1) is stirred at 50° C. for 12 hours. The reaction mixture is then pored on water (150 mL). The aqueous phase is extracted with ethyl acetate (3×100 mL). The combined organic layers are washed with water (3×200 mL). The organic phase is dried over magnesium sulfate and evaporated under vacuum to afford the title compound.

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers are washed with water (3×200 mL)
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-30d32df0c1424bf0ad21d0d8f6e1c3ec
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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