Tetrahydrofuran → 3-((1H-1,2,4-triazol-5-yl)methyl)-6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridine

HRID 455129Notes

Reaction equation

HRID 455129 reaction equation
C1COCC1.[F:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:13]([CH2:23][C:24]3[N:28](C=C)[N:27]=[CH:26][N:25]=3)=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:15]=2)[CH:12]=1.[BH4-].[Na+]>O.[OH-].[Na+].[Hg]>[NH:28]1[C:24]([CH2:23][C:13]2[N:11]3[CH:12]=[C:7]([F:6])[CH:8]=[CH:9][C:10]3=[N:15][C:14]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:25][CH:26]=[N:27]1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 670288936-fluoro-2-(4-fluorophenyl)-3-((1-vinyl-1H-1,2,4-triazol-5-yl)methyl)imidazo[1,2-a]pyridine

Product 1

HCID 670290043-((1H-1,2,4-triazol-5-yl)methyl)-6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridineYield 30%

Reagents, catalysts & solvents 3

HCID 23931MercuryCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of mercuric trifluroacetate (128 mg, 0.30 mmol) in 0.3 mL of water was added 0.3 mL of THF. The yellow suspension thus formed was mled to 0° C., and 6-fluoro-2-(4-fluorophenyl)-3-((1-vinyl-1H-1,2,4-triazol-5-yl)methyl)imidazo[1,2-a]pyridine (101 mg, 0.30 mmol) was added portion wise. After the addition was over, the reaction mixture was allowed to warm to room temperature and stirred for 12 h. After cooling to 0° C., 0.3 mL of 3 N NaOH followed by 0.3 mL of 0.5 M NaBH4 in 3 N NaOH was added to the mixture. The mercury was allowed to settle, and the supernatant liquid decanted and extracted with CH2CH2. The extract was dried over anhydrous Na2SO4 and concentrated to give the crude product which was purified silica gel chromatography. 28 mg, 30% yield. m/e+=312 (M+H+). 1H-NMR (400 MHz, CD3OD, δ): 8.41 (m, 1H), 8.33 (s, 1H), 7.79 (m, 2H), 7.60 (m, 1H), 7.33 (m, 1H), 7.21 (m, 2H), 4.53 (s, 2H).

Workup

  1. customThe yellow suspension thus formed
  2. customwas mled to 0° C.
  3. additionAfter the addition
  4. temperatureAfter cooling to 0° C.
  5. additionwas added to the mixture
  6. customthe supernatant liquid decanted
  7. extractionextracted with CH2CH2
  8. dry with materialThe extract was dried over anhydrous Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f378381e43e34e5ca9568be064a4371f
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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