Lithium borohydride → HCID 67067759, compound

HRID 1037288Notes

Reaction equation

HRID 1037288 reaction equation
C[O:2][C:3]([C:5]1[C:13]([O:14][CH3:15])=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[S:16](=[O:21])(=[O:20])[N:17]([CH3:19])[CH3:18])=[CH:7][CH:6]=1)=O.[BH4-].[Li+]>C1COCC1>[CH3:19][N:17]([CH3:18])[S:16]([N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([CH2:3][OH:2])[C:13]=2[O:14][CH3:15])[CH:9]=[N:10]1)(=[O:20])=[O:21]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67067770HCID 67067770, compound

Product 1

HCID 67067759HCID 67067759, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-dimethylsulfamoyl-7-methoxy-1H-indazole-6-carboxylic acid methyl ester (6.23 g, 19.9 mmol) in anhydrous THF (100 mL) at 0° C. under an atmosphere of nitrogen was added lithium borohydride solution (2 M in THF, 39.8 mL, 79.5 mmol) and the mixture was allowed to reach RT with stirring. After 68 h, the mixture was quenched with saturated aqueous ammonium chloride solution (40 mL) and water (80 mL) and extracted with EtOAc (50 mL). The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford the title compound as an oil (5.58 g, 98%). LCMS (Method G): RT=2.73 min, [M+H]+=286.

Workup

  1. customto reach RT
  2. customthe mixture was quenched with saturated aqueous ammonium chloride solution (40 mL) and water (80 mL)
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-355ef8aefcb14147bdafb9cbc0c6be57
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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