Sodium hydride → HCID 68554957, compound

HRID 2381897Notes

Reaction equation

HRID 2381897 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH3:13].[NH2:14]OS(O)(=O)=O>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH2:14])[CH:8]=[C:7]2[CH3:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76284hydroxylamine-O-sulfonic acidHCID 223515035-Fluoro-3-methyl-1H-indole

Product 1

HCID 68554957HCID 68554957, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of NaH (2.01 g, 50.3 mmol, 60% in mineral oil) in DMF (45 mL) at 0° C. is treated with 5-fluoro-3-methyl-1H-indole (500 mg, 3.55 mmol), and the mixture is stirred at 0° C. for 1 h. NH2OSO3H (1.9 g, 16.75 mmol) is added portion wise, and the mixture is then warmed to rt and stirred for 2 h. The mixture is quenched with MeOH, diluted with water, extracted with EtOAc, dried (Na2SO4), filtered and concentrated to afford 5-fluoro-3-methyl-indol-1-ylamine. MS: 165 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.22 (s, 3H), 6.86 (m, 1H), 6.99 (s, 1H), 7.08 (m, 1H), 7.36 (m, 1H).

Workup

  1. temperaturethe mixture is then warmed to rt
  2. stirringstirred for 2 h
  3. customThe mixture is quenched with MeOH
  4. additiondiluted with water
  5. extractionextracted with EtOAc
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d56156cb334548da9c53c40852e94f97
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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