Hydrochloric Acid → HCID 178520033, compound

HRID 2064648Notes

Reaction equation

HRID 2064648 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)+.

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-29dced371895469eab2bd21bacc6e213
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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