Sodium sulfate decahydrate → (6-Fluoro-imidazo[1,5-a]pyridin-3-yl)-methanol

HRID 245852Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:9]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]2=[CH:7][N:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:14][C:11]1[CH:12]=[CH:13][C:8]2[N:9]([C:5]([CH2:3][OH:2])=[N:6][CH:7]=2)[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a round-bottomed flask, 6-fluoro-imidazo[1,5-a]pyridine-3-carboxylic acid methyl ester (223 mg, 1.15 mmol) was dissolved in THF (7 ml). The solution was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 1.4 ml, 1.4 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 h then sodium sulfate decahydrate was carefully added. When gas evolution had ceased, the ice bath was removed, sodium sulfate was added and the mixture was stirred vigorously for 30 min at room temperature. The suspension was filtered over Celite and rinsed with ethyl acetate and methanol. The filtrate was concentrated to give 225 mg of (6-fluoro-imidazo[1,5-a]pyridin-3-yl)-methanol as a brown solid which was used without further purification.

Workup

customthe ice bath was removed
additionsodium sulfate was added
stirringthe mixture was stirred vigorously for 30 min at room temperature
filtrationThe suspension was filtered over Celite
washrinsed with ethyl acetate and methanol
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-ce62fafcdac44e42b410d73225d1caaf
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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