Potassium Carbonate → 2-Phenylisonicotinic acid

HRID 528683Notes

Reaction equation

HRID 528683 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>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:17]1([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=2)[C:5]([OH:7])=[O:6])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 2227012-Bromoisonicotinic acid

Product 1

HCID 27628452-Phenylisonicotinic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

2-bromoisonicotinic acid (0.210 g, 1.040 mmol) was dissolved in degassed DME (Volume: 8 ml) under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.060 g, 0.052 mmol) was added, the resulting reaction mixture was stirred for 15 min. Then aqueous potassium carbonate (4.16 ml, 8.32 mmol) and phenylboronic acid (0.171 g, 1.403 mmol) were added subsequently. The resulting RM was refluxed at 95° C. for 18 h and then cooled to rt. After filtration over celite the reaction mixture was acidified to pH 3-4 and the white precipitate was filtered off and washed with water

Workup

  1. customthe resulting reaction mixture
  2. temperaturecooled to rt
  3. filtrationAfter filtration over celite the reaction mixture
  4. filtrationthe white precipitate was filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-71a99dc2165a42a594c1c4e172af87b2
Source dataset
uspto-grants-2016_05
Patent number
US09346814B2

Reaction notes

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