1H-Pyrrolo(2,3-b)pyridine → 1H-Pyrrolo[2,3-b]pyridin-1-amine

HRID 2382004Notes

Reaction equation

HRID 2382004 reaction equation
[NH:1]1[C:5]2=[N:6][CH: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=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 25423MonochloramineHCID 23665647Potassium tert-butoxide

Product 1

HCID 52239501H-Pyrrolo[2,3-b]pyridin-1-amineYield 31%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of pyrrolo[2,3-b]pyridine (16.9 mmol) and potassium tert-butoxide (33.8 mmol) in DMF (76 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl in ether (169.2 mL) is added drop-wise at rt and the reaction mixture is stirred at rt for 2 h. The reaction mixture is quenched with 5% Na2S2O3 aqueous solution (100 mL), and extracted with ether for three times. The combined organic layer is washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 60-80% EtOAc in heptane to afford pyrrolo[2,3-b]pyridin-1-ylamine (703 mg, 31%) as a solid. MS: 134 (M+H); 1H NMR (300 MHz, CDCl3): δ 5.04 (br, 2N—H), 6.35 (d, H), 7.09 (m, H), 7.35 (m, H), 7.91 (m, H), 8.34 (d, H).

Workup

  1. customThe reaction mixture is quenched with 5% Na2S2O3 aqueous solution (100 mL)
  2. extractionextracted with ether for three times
  3. washThe combined organic layer is washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 60-80% EtOAc in heptane

Sources & evidence

ORD record
ord-1a060dd59f7d47708996593774160f26
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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