5-(Trifluoromethyl)pyridin-2-ylamidoxime → 2-[5-(3-Bromo-furan-2-yl)-[1,2,4]oxadiazol-3-yl]-5-trifluoromethyl-pyridine

HRID 2114935Notes

Reaction equation

HRID 2114935 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([C:9](=[N:11][OH:12])[NH2:10])=[N:7][CH:8]=1.[Br:15][C:16]1[CH:20]=[CH:19][O:18][C:17]=1[C:21](Cl)=O>>[Br:15][C:16]1[CH:20]=[CH:19][O:18][C:17]=1[C:21]1[O:12][N:11]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:13])[F:14])=[CH:8][N:7]=2)[N:10]=1

Participants

3

Reactant 2

HCID 27793275-(Trifluoromethyl)pyridin-2-ylamidoximeHCID 218645763-Bromofuran-2-carbonyl chloride

Product 1

HCID 102919892-[5-(3-Bromo-furan-2-yl)-[1,2,4]oxadiazol-3-yl]-5-trifluoromethyl-pyridine

Procedure

The title compound was prepared from 5-trifluoromethyl-pyridine-2-amidoxime (480 mg, 2.34 mmol) and 3-bromo-furan-2-carbonyl chloride (490 mg, 2.34 mmol) similar to Example 16, and yielded 718 mg (85%) of light yellow solid. 1H NMR (CDCl3): 9.09 (m, 1H), 8.37 (d, J=8.24 Hz, 1H), 8.14 (dd, J=8.10, 2.34 Hz, 1H), 7.70 (d, J=1.92 Hz, 1H), 6.78 (d, J=1.92 Hz, 1H).

Workup

  1. customyielded 718 mg (85%) of light yellow solid

Sources & evidence

ORD record
ord-ce4e21f5ccff4fba93ed67b3db68469f
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Reaction notes

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