3-ISOPROPYL-[1,2,4]TRIAZOLO[4,3-A]PYRIDINE-6-CARBALDEHYDE → α-(4-Fluorophenyl)-3-(1-methylethyl)-1,2,4-triazolo[4,3-a]pyridine-6-methanol

HRID 2252321Notes

Reaction equation

HRID 2252321 reaction equation
[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([CH:13]=[O:14])[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([Mg]Br)=[CH:18][CH:17]=1>C1COCC1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH:13]([C:10]2[CH:11]=[CH:12][C:7]3[N:8]([C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]=3)[CH:9]=2)[OH:14])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 115719333-ISOPROPYL-[1,2,4]TRIAZOLO[4,3-A]PYRIDINE-6-CARBALDEHYDEHCID 178418676HCID 178418676, compound

Product 1

HCID 17974498α-(4-Fluorophenyl)-3-(1-methylethyl)-1,2,4-triazolo[4,3-a]pyridine-6-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine-6-carbaldehyde (404.6 mg, 2.13 mmol) in THF (8 mL) at ambient temperature was added 4-fluorophenylmagnesium bromide (3 mL, 1.0 M in THF). The resulting reaction was stirred for 20 hours, then quenched with water, followed by saturated NaHCO3. The reaction mixture was extracted with ethyl acetate, the organics dried over sodium sulfate, and concentrated to give the above named compound (591.3 mg, 97%).

Workup

  1. customThe resulting reaction
  2. customquenched with water
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialthe organics dried over sodium sulfate
  5. concentrationconcentrated
  6. customto give the

Sources & evidence

ORD record
ord-3b480be61e4749e68e315b9207d279c9
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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