Sodium hydride → HCID 68553177, compound

HRID 2382096Notes

Reaction equation

HRID 2382096 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH2:13]OS(O)(=O)=O>CN(C=O)C>[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[N:6]([NH2:13])[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76284hydroxylamine-O-sulfonic acidHCID 213006013-Methyl-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 68553177HCID 68553177, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

60% Sodium hydride (6.69 g, 167 mmol) is added to a stirred solution of 3-methyl-1H-pyrrolo[2,3-c]pyridine (1.47 g, 11.2 mmol) in DMF (33 mL) portion wise at 0° C. for 1 h. Hydroxylamine-O-sulfonic acid (6.3 g, 55.8 mmol) is added in portions at 0° C. and stirred for 2 h at 0° C. The reaction mixture is quenched at 0° C. with water, concentrated in vacuo to remove DMF. The residue is triturated in DCM. The solid is filtered off and the filtrate is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10% MeOH in DCM to afford 3-methyl-pyrrolo[2,3-c]pyridin-1-ylamine (1 g, 61%). MS: 148 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.85 (s, 1H), 8.27 (d, 1H), 7.46 (d, 1H), 7.09 (s, 1H), 2.30 (s, 3H).

Workup

  1. customThe reaction mixture is quenched at 0° C. with water
  2. concentrationconcentrated in vacuo
  3. customto remove DMF
  4. customThe residue is triturated in DCM
  5. filtrationThe solid is filtered off
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 10% MeOH in DCM

Sources & evidence

ORD record
ord-16c0c5c318ab48f7b143e39e24c3c5ca
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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