Sodium Hydroxide → HCID 10296995, compound

HRID 1168223Notes

Reaction equation

HRID 1168223 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:16]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23](Br)=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=3)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:5][CH:4]=1.[CH2:31]([Sn](CCCC)(CCCC)C#CC)[CH2:32][CH2:33]C.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:16]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:31]#[C:32][CH3:33])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=3)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 10277541HCID 10277541, compound

Product 1

HCID 10296995HCID 10296995, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of 2-[(6-Methoxypyrid-3-yl)methylamino]-N-[4-bromo-3-(trifluoromethyl)phenyl]-3-pyridinecarboxamide (Example 24; 0.96 g, 2.0 mmol) in dry toluene (50 mL) is purged with argon for 20 minutes at 40° C. Tributyl-l-propynylstannane (1.0 g, 2.4 mmol) and tetrakis-(triphenylphosphine)palladium (0) (60 mg) are then added and the resulting mixture is heated at 100° C. for 30 hours under an argon atmosphere. The mixture is then cooled, treated with an aqueous solution of sodium hydroxide (20 mL of 0.1 M) and purged with air for 2 hours. The resulting mixture is then diluted with ethylacetate (200 mL). The orgainic phase is then sequentially washed with water (2×40 mL) and saturated aqueous sodium chloride (1×40 mL), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 50% ethyl acetate in hexane and recrystallised from ether-hexane to give the tite compound as a pale-yellow crystalline solid, m.p. 109-111° C.

Workup

  1. temperatureThe mixture is then cooled
  2. custompurged with air for 2 hours
  3. additionThe resulting mixture is then diluted with ethylacetate (200 mL)
  4. washThe orgainic phase is then sequentially washed with water (2×40 mL) and saturated aqueous sodium chloride (1×40 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure
  8. customto yield the crude product which
  9. customis purified by column chromatography on silica gel, eluent 50% ethyl acetate in hexane
  10. customrecrystallised from ether-hexane

Sources & evidence

ORD record
ord-d003ce168670464fae0b92c61d75e73b
Source dataset
uspto-grants-2003_09
Patent number
US06624174B2

Reaction notes

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