1-Butyne → 2-But-1-ynyl-4-fluorophenylamine

HRID 1751794Notes

Reaction equation

HRID 1751794 reaction equation
O1[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9](I)[CH:8]=1.C#CCC>[Cu](I)I.C(N(CC)CC)C>[C:2]([C:11]1[CH:12]=[C:7]([F:6])[CH:8]=[CH:9][C:10]=1[NH2:13])#[C:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 78461-ButyneHCID 8028TetrahydrofuranHCID 27782834-Fluoro-2-iodoaniline

Product 1

HCID 580803722-But-1-ynyl-4-fluorophenylamine

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8471TriethylamineSolvent

Procedure

80 ml of tetrahydrofuran is placed under argon. 5 g 4-fluoro-2-iodophenylamine, 0.74 g dichlorobis(triphenylphosphine) palladium(II), 0.2 g copper iodide and 8.8 ml triethylamine are added. 4 g gaseous 1-butyne are passed through the suspension. The reaction mixture is stirred under argon for 15 hours at ambient temperature, then filtered through Celite and evaporated to dryness. 3.4 g product are obtained in the form of a solid. 1H NMR (400 MHz, DMSO): 2.45 (2H, q); 1.18 (3H, t).

Workup

  1. filtrationfiltered through Celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-72be47ac980441c8a82a26bc0fd26d7d
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

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