Potassium Carbonate → HCID 53647853, compound

HRID 581959Notes

Reaction equation

HRID 581959 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12](I)[CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2].C(B(CC)[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)C.C(=O)([O-])[O-].[K+].[K+]>O.C(COC)OC.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]([C:3]1[CH:18]=[CH:17][C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 54293958HCID 54293958, compound

Product 1

HCID 53647853HCID 53647853, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (31) (4 g, 11.6 mmol), diethyl 3-pyridylborane (2.04 g, 13.9 mmol), potassium carbonate (4.8 g, 34.8 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in a mixture of water (20 ml) and dimethoxyethane is stirred at 80° C. in a nitrogen atmosphere overnight. After cooling the resulting suspension is poured into water and the crude product is filtered off, washed with water and dried. Purification is achieved by column-chromatography on silica gel using a mixture of ethyl acetete and methanol (9:1) as the eluent. Yield 2.46 g (72%) of the title compound. Mp.191-193° C.

Workup

  1. temperatureAfter cooling the resulting suspension
  2. filtrationthe crude product is filtered off
  3. washwashed with water
  4. customdried
  5. customPurification
  6. additiona mixture of ethyl acetete and methanol (9:1) as the eluent

Sources & evidence

ORD record
ord-a68e964765124bc8a36bd033aafdd0e9
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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