3-(3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl)benzonitrile → HCID 67026083, compound

HRID 713797Notes

Reaction equation

HRID 713797 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[O:9][N:8]=2)[CH:2]=1.C[Si](C)(C)[O-:22].[K+]>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]([NH2:16])=[O:22])[O:9][N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 119981803-(3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl)benzonitrileHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 67026083HCID 67026083, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 1 (248 mg, 1 mmol) in THF (10 ml) was stirred with potassium trimethylsilanolate (257 mg, 2.000 mmol) at 65° C. for 10 hours. It was then quenched with water (20 mL) and stirred at ambient temperature for 2 hours. The precipitate was filtered and dried under vacuum to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.67 (ddd, J=7.9, 4.8, 0.8 Hz, 1H), 7.78 (t, J=7.7 Hz, 1H), 8.23 (dt, J=8.1, 1.4, 1.2 Hz, 1H), 8.30 [s (broad, 2H], 8.36 (dt, J=8.1, 1.3 Hz, 1H), 8.48 (dt, J=7.9, 2.0 Hz, 1H), 8.68-8.73 (m, 1H), 8.83 (dd, J=4.8, 1.6 Hz, 1H), 9.28 (dd, J=2.2, 1.0 Hz, 1H) ppm; MS (DCl/NH3) m/z 267 (M+H)+.

Workup

  1. customIt was then quenched with water (20 mL)
  2. filtrationThe precipitate was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-0d86f54c8e1648d2881894e068ef598a
Source dataset
uspto-grants-2015_11
Patent number
US09186407B2

Reaction notes

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