1-Butyne → 2-But-1-ynyl-5-fluoro-phenylamine

HRID 1640247

Reaction equation

HRID 1640247 reaction equation
[CH2:1]1[CH2:5]O[CH2:3][CH2:2]1.[F:6][C:7]1[CH:8]=[CH:9][C:10](I)=[C:11]([CH:13]=1)[NH2:12].C(N(CC)CC)C.C#CCC>C(OCC)C.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.[Cu](I)I>[C:5]([C:10]1[CH:9]=[CH:8][C:7]([F:6])=[CH:13][C:11]=1[NH2:12])#[C:1][CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 78461-ButyneHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 27745125-Fluoro-2-iodoaniline

Product 1

HCID 581174762-But-1-ynyl-5-fluoro-phenylamine

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

160 mL of THF were placed in the flask and degassed with argon. Then 10 g (45 mmol) 5-fluoro-2-iodo-aniline, 1.5 g (2.1 mmol) PdCl2(PPh3)2 and 0.40 g (2.1 mmol) copper iodide were added and the flask was rinsed with argon. Then 18 mL (0.13 mol) triethylamine were added and 3.0 g (55 mmol) 1-butyne (in gaseous form) were passed through the solution. The reaction mixture was stirred for 3 h at RT, then diluted with diethyl ether, filtered through kieselguhr and evaporated down.

Workup

  1. customdegassed with argon
  2. washthe flask was rinsed with argon
  3. filtrationfiltered through kieselguhr
  4. customevaporated down

Sources & evidence

ORD record
ord-db4a19ae8e89483987734dd1bd3132c5
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Linked notes

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