Azidotrimethylsilane → HCID 178505599, compound

HRID 431978Notes

Reaction equation

HRID 431978 reaction equation
C[Al](C)C.C[Si]([N:9]=[N+:10]=[N-:11])(C)C.[C:12]([C:14]1[CH:15]=[C:16]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=3)[N:22]=2)[CH:17]=[C:18]([F:20])[CH:19]=1)#[N:13]>C1(C)C=CC=CC=1>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]2[N:22]=[C:21]([C:16]3[CH:15]=[C:14]([C:12]4[NH:13][N:11]=[N:10][N:9]=4)[CH:19]=[C:18]([F:20])[CH:17]=3)[O:25][N:24]=2)=[N:27][CH:28]=1

Participants

5

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 98387293-Fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrileHCID 16682925Trimethylaluminum

Product 1

HCID 178505599HCID 178505599, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2 M trimethylaluminum (0.45 mL, 0.9 mmole, toluene) with toluene (1 mL) at 10° C., trimethylsilyl azide (0.119 mL, 0.9 mmole) was added, followed by the addition of 5-(3-cyano-5-fluorophenyl)-3-(5-fluoro-pyrid-2-yl)-1,2,4-oxadiazole. The reaction was heated at 80° C. for 2 hours and then quenched with 6 N hydrochloride (2 mL) and solid was collected by filtration. The product was recrystallized with dimethylformamide to give 59 mg (36%) of 3-(5-fluoro-pyrid-2-yl)-5-[3-fluoro-5-(1H-tetraazol-5-yl)-phenyl]-1,2,4-oxadiazole. 1H-NMR (DMSO-d 6), δ (ppm): 8.83 (d, 1H), 8.70 (s, 1H), 8.31 (m, 1H), 8.10 (m, 2H), 8.04 (dt, 1H).

Workup

  1. customquenched with 6 N hydrochloride (2 mL) and solid
  2. filtrationwas collected by filtration
  3. customThe product was recrystallized with dimethylformamide

Sources & evidence

ORD record
ord-6f59777b16944cf1a35970edc7e29e63
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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