Sodium hydride → HCID 68555047, compound

HRID 2381946Notes

Reaction equation

HRID 2381946 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([CH3:15])([OH:14])[CH3:13].[H-].[Na+].[NH2:18]OS(O)(=O)=O>CN(C=O)C.CCOC(C)=O>[NH2:18][N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[C:5]([CH2:11][C:12]([CH3:15])([OH:14])[CH3:13])=[CH:6]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76284hydroxylamine-O-sulfonic acidHCID 68554254HCID 68554254, compound

Product 1

HCID 68555047HCID 68555047, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(5-fluoro-1H-indol-3-yl)-2-methyl-propan-2-ol (207 mg, 1 mmol) in DMF (10 mL) is cooled to 0° C., treated with NaH (600 mg, 15 mmol, 60% in mineral oil) and stirred for 30 min. H2NOSO3H (565 mg, 5 mmol) is added portion wise, and the mixture is warmed to rt over 2 h. The mixture is diluted with EtOAc (100 mL), quenched with water, extracted with EtOAc, dried (Na2SO4), filtered and concentrated in vacuo to afford 1-(1-amino-5-fluoroindol-3-yl)-2-methyl-propan-2-ol, which is used in the next step without further purification.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b52c03812bb41cb96b10b97dd3b810d
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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