6-Azaindole → HCID 68555938, compound

HRID 2382016Notes

Reaction equation

HRID 2382016 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].[NH2:16]Cl>CN(C=O)C.CCOCC>[N:1]1([NH2:16])[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 92196-AzaindoleHCID 25423MonochloramineHCID 23665647Potassium tert-butoxide

Product 1

HCID 68555938HCID 68555938, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of pyrrolo[2,3-c]pyridine (8.47 mmol) and potassium tert-butoxide (16.9 mmol) in DMF (38 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl in ether (84.6 mL) is added drop-wise at rt, and the reaction mixture is stirring at rt for 2 h., quenched with 5% Na2S2O3 aqueous solution (10 mL), and extracted with ether. The organic layer is separated, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-10% MeOH in DCM to afford pyrrolo [2,3-c]pyridin-1-ylamine (226 mg, 11%) as a solid. MS: 134 (M+H); 1H NMR (300 MHz, CDCl3): δ 4.96 (br, 2N—H), 6.43 (d, H), 7.29 (m, H), 7.50 (d, H), 8.29 (d, H), 8.89 (s, H).

Workup

  1. customquenched with 5% Na2S2O3 aqueous solution (10 mL)
  2. extractionextracted with ether
  3. customThe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel chromatography
  9. washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-f0d87b356d094617b45613ef4d8ca6b0
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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