Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [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
Reactant: CC(C)(O)Cc1c[nH]c2ccc(F)cc12
Reactant: NOS(=O)(=O)O
Agent: [H-]
Agent: [Na+]
Solvent: CCOC(C)=O
Solvent: CN(C)C=O
Product: CC(C)(O)Cc1cn(N)c2ccc(F)cc12
Temperature: 25 °C
Reaction time: 0.5 h

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.