Hydrochloric Acid → HCID 178520033, compound

HRID 2182394Notes

Reaction equation

HRID 2182394 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11](O)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH2:11][OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24436Sodium SulfateHCID 149990525-fluoro-1H-indazole-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 178520033HCID 178520033, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-fluoro-1H-indazole-3-carboxylic acid [0.680 g, Reference Example 26(a)] in anhydrous tetrahydrofuran (15 ml), at 0° C., was treated portionwise with lithium aluminium hydride (0.716 g), then stirred for 2 hours at ambient temperature and then treated with saturated aqueous sodium sulfate. The reaction mixture was acidified by addition of hydrochloric acid (1N) and then extracted three times with ethyl acetate (30 ml). The combined organic extracts were dried over magnesium sulfate and then evaporated. The residual dark brown oil was subjected to flash column chromatography on silica eluting with a mixture of 40/60 petrol and ethyl acetate (1:1 to 1:3 v/v) to yield (5-fluoro-1H-indazol-3-yl)-methanol (0.144 g) as a brown solid. LC-MS (METHOD B): RT=2.40 minutes; 167 (M+H)+. (b) (6-Fluoro-1H-indazol-3-yl)-methanol

Workup

  1. extractionextracted three times with ethyl acetate (30 ml)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customevaporated
  4. additionThe residual dark brown oil was subjected to flash column chromatography on silica eluting with a mixture of 40/60 petrol and ethyl acetate (1:1 to 1:3 v/v)

Sources & evidence

ORD record
ord-95dce89a5efb479f98c7aedc4cf4817d
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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