Ammonia → 4-Benzyl-5-bromo-2-(3-hydroxy-1-butynyl)pyridine

HRID 1359390Notes

Reaction equation

HRID 1359390 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([Br:20])=[CH:9][N:8]=1)(=O)=O.[CH:23]#[C:24][CH:25]([OH:27])[CH3:26].C(N(CC)CC)C.N>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.CN(C)C=O>[CH2:13]([C:11]1[C:10]([Br:20])=[CH:9][N:8]=[C:7]([C:23]#[C:24][CH:25]([OH:27])[CH3:26])[CH:12]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 181821814-Benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate

Product 1

HCID 181823824-Benzyl-5-bromo-2-(3-hydroxy-1-butynyl)pyridineYield 79%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

650 mg of 4-benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate (Production Example 1), 115 mg of 1-butyne-3-ol, 100 mg of tetrakis(triphenylphosphine)palladium(0), 30 mg of cuprous iodide and 1 ml of triethylamine were mixed with 5 ml of N,N-dimethylformamide, followed by stirring for one hour in an oil bath kept at 60° C. After cooling as it was, aqueous ammonia was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with brine and then evaporated. The residue was subjected to silica gel column chromatography and eluted with 30% ethyl acetate/hexane, to give 410 mg of the target compound.

Workup

  1. customkept at 60° C
  2. temperatureAfter cooling as it
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. customevaporated
  6. washeluted with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1dd072695ddb49ac9e1f3f4994eb8c26
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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