Hydrazine → 1-methyl-1H-pyrrolo[2,3-b]pyridin-6-amine

HRID 1396365Notes

Reaction equation

HRID 1396365 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:9][CH:10]=[C:5]2[CH:4]=[CH:3]1.NN>C(O)C>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([NH2:11])=[CH:9][CH:10]=[C:5]2[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 866897272-(1-methyl-1H-pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dione

Product 1

HCID 866897281-methyl-1H-pyrrolo[2,3-b]pyridin-6-amineYield 98.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(1-Methyl-1H-pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dione (220 mg, 0.793 mmol) was dissolved in ethanol (4 mL), then hydrazine (0.5 mL, 15.9 mmol) was added. After 16 h, the mixture was concentrated in vacuo and partitioned between ethyl acetate and water. The aqueous layer was extracted twice more with ethyl acetate, then the combined organic extracts were washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo. Purification by chromatography (silica, 10 to 50% ethyl acetate in hexanes) gave 1-methyl-1H-pyrrolo[2,3-b]pyridin-6-ylamine (115 mg, 98%) as an off-white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.67 (d, J=8.3 Hz, 1H) 6.87 (d, J=3.4 Hz, 1H) 6.35 (d, J=8.3 Hz, 1H) 6.30 (d, J=3.4 Hz, 1H) 4.38 (br. s., 2H) 3.76 (s, 3H); LCMS (EI/CI) m/z: 148 [M+H].

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted twice more with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography (silica, 10 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-537f6aeb7e2f4042b6f242c11eb54b15
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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