2-Iodophenylacetonitrile → [2-(5-Methyl-3-phenyl-isoxazol-4-ylethynyl)-phenyl]-acetonitrile

HRID 1984653Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][O:6][C:7]=1[CH3:8])#[CH:2].I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]#[N:24]>>[CH3:8][C:7]1[O:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]=1[C:1]#[C:2][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]#[N:24]

Participants

Reactant 2

HCID 44022822-Iodophenylacetonitrile

HCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazole

Product 1

HCID 68853004[2-(5-Methyl-3-phenyl-isoxazol-4-ylethynyl)-phenyl]-acetonitrileYield 87%

Procedure

As described for example 11c, 4-ethynyl-5-methyl-3-phenyl-isoxazole (110 mg, 0.60 mmol) was converted (using 2-iodo-phenylacetonitrile instead of 2-chloro-4-iodopyridine) to the title compound (SiO2, heptane:ethyl acetate=100:0 to 80:20, 156 mg, 87%) which was obtained as a light brown oil. MS: m/e=375.1 [M+H]+.

Sources & evidence

ORD record: ord-761998d8b7414e7a914e36b24a2abae0
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544704B2

Reaction notes

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