Triethylamine → HCID 18511691, compound

HRID 1370593Notes

Reaction equation

HRID 1370593 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:10]1([C:16]#[CH:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.O.CCOC(C)=O>CN(C=O)C.[Cu]Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:6]1[CH:7]=[C:2]([C:17]#[C:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([NH2:9])=[N:4][CH:5]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 27639713-Bromo-5-chloropyridin-2-amineHCID 22728543Water ethylacetate

Product 1

HCID 18511691HCID 18511691, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-5-chloro-2-pyridinamine (414 mg, 2.0 mmol), phenyl acetylene (225 mg, 2.2 mmol), copper (I) chloride (16 mg, 0.16 mmol), triethylamine (555 μl, 4.0 mmol) and dichlorobis(triphenylphosphine)palladium (II) (32 mg, 0.05 mmol) in DMF (0.5 ml) in a teflon pressure vessel was heated in a microwave (full power) for 30 sec, allowed to cool to RT and reheated for a further 30 sec. After cooling to RT, the reaction mixture was partioned between water—EtOAc. and the organic phase washed with sat. brine, dried over MgSO4, and concentrated. Purification by column chromatography on silica gel eluting with methylene chloride—methanol (99:1) and subsequent crystallisation from hexane gave the title compound as a yellow solid (130 mg, 0.6 mmol):

Workup

  1. temperatureAfter cooling to RT
  2. washand the organic phase washed with sat. brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel eluting
  6. customwith methylene chloride—methanol (99:1) and subsequent crystallisation from hexane

Sources & evidence

ORD record
ord-9af1969663da4117bb04f2b5890d6ac8
Source dataset
uspto-grants-2003_06
Patent number
US06583162B1

Reaction notes

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