Nitrogen → (1H-Pyrrolo[2,3-b]pyridin-2-yl)methanamine

HRID 1890533Notes

Reaction equation

HRID 1890533 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([NH2:12])=O.N#N.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH2:10][NH2:12]

Participants

5

Reactant 3

HCID 947NitrogenHCID 21226445Aluminium lithium hydrideHCID 446081041H-Pyrrolo[2,3-b]pyridine-2-carboxamide

Product 1

HCID 67305381(1H-Pyrrolo[2,3-b]pyridin-2-yl)methanamineYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1H-pyrrolo[2,3-b]pyridine-2-carboxamide (H-2) (805 mg, 5.0 mmol) in dried THF (10 mL) at 0° C. under 1 atm of N2 was slowly added LiAlH4 (570 mg, 15 mmol). The mixture was stirred at 80° C. overnight. The mixture was then cooled to 0° C. concentrated, and then purified by chromatography on silica gel to afford the title compound (720 mg). MS (m/z): 148 (M+1)+.

Workup

  1. customat 0° C.
  2. temperatureThe mixture was then cooled to 0° C.
  3. concentrationconcentrated
  4. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-91d2a3ca036643b9a15130922d70ea83
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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