Hydrochloric Acid → HCID 68693732, compound

HRID 2354061Notes

Reaction equation

HRID 2354061 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:5]([OH:7])=[O:6].[C:12]1(/[CH:18]=[CH:19]/B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].Cl>CC#N.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2](/[CH:19]=[CH:18]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acidHCID 5702628Styrylboronic acid

Product 1

HCID 68693732HCID 68693732, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2-chloro-6-methyl-isonicotinic acid (171.6 mg, 1 mmol), (E)-2-phenyl-etheneboronic acid (180.0 mg, 1.2 mmol), K2CO3 (414 mg), Pd(dppf)Cl2-CH2Cl2 (27 mg) in CH3CN—H2O (3:1, 10 mL) is stirred under argon at 90° C. for 15 h. The solution is cooled to r.t. and aq. hydrochloric acid (2 M, 1.5 mL) is added to adjust the pH at 3. The mixture is evaporated to dryness and purified by reversed phase MPLC to provide the title compound.

Workup

  1. temperatureThe solution is cooled to r.t.
  2. customThe mixture is evaporated to dryness
  3. custompurified by reversed phase MPLC

Sources & evidence

ORD record
ord-8fb8509910584883ad235b36d1bfcf3d
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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