Triethylamine → HCID 19434138, compound

HRID 1735712Notes

Reaction equation

HRID 1735712 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][O:11][C:10]([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=3[F:21])=[N:9]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]#[CH:49])=[CH:44][CH:43]=1.C(N(CC)CC)C>ClCCl.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.[Cu]I>[F:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([F:20])[C:14]=1[C:10]1[O:11][CH2:12][CH2:13][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:49]#[C:48][C:45]3[CH:46]=[CH:47][C:42]([F:41])=[CH:43][CH:44]=3)=[CH:3][CH:4]=2)[N:9]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 5226271-Ethynyl-4-fluorobenzeneHCID 19434136HCID 19434136, compound

Product 1

HCID 19434138HCID 19434138, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In 2 mL of dichloromethane, the product of Step C (0.07 g) was combined with tetrakis(triphenylphosphine)palladium(0) (0.010 g), copper(I) iodide (0.006 g), triphenylphosphine (0.006 g), (4-fluorophenyl)acetylene (prepared by the method of A.D. Allen and C. D. Cook, Can. J. Chem. (1963), 41, 1084; 0.15 g), and triethylamine (2 mL) and the mixture heated at reflux until thin layer chromatographic analysis showed consumption of starting material. The mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title product, a compound of this invention, as a solid melting at 95°-110° C. (material prepared on larger scale, identical by 1H NMR spectroscopy, was recrystallized from ethyl acetate/hexane to give a solid melting at 102°-104° C.). 1H NMR (CDCl3) δ2.0 (m, 1H), 2.4 (m, 1H), 4.3 (m, 1H), 4.5 (m, 1H), 4.8 (m, 1H), 6.9-7.1 (m,4H), 7.3-7.4 (m,3H), 7.5-7.6 (m,4H).

Workup

  1. customprepared by the method of A.D
  2. temperatureat reflux until thin layer chromatographic analysis
  3. customconsumption of starting material
  4. concentrationThe mixture was concentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-842874233d864a00beaccb5ea924bcaa
Source dataset
uspto-grants-1996_07
Patent number
US05538967

Reaction notes

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