Diethyl Ether → 1-(5-(1-Aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)azetidin-3-ol

HRID 75311Notes

Reaction equation

HRID 75311 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:7]=[C:8]3[N:16]([CH3:17])[CH:15]=[CH:14][C:9]3=[N:10][C:11]=2[C:12]#[N:13])[CH2:3]1.[CH3:18][Mg]Br.CCOCC.[BH4-].[Na+]>C1COCC1>[NH2:13][CH:12]([C:11]1[N:10]=[C:9]2[CH:14]=[CH:15][N:16]([CH3:17])[C:8]2=[CH:7][C:6]=1[N:4]1[CH2:5][CH:2]([OH:1])[CH2:3]1)[CH3:18]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 867080096-(3-Hydroxyazetidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 867080101-(5-(1-Aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)azetidin-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(3-hydroxyazetidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (2.6 g, 11 mmol) in THF 100 mL at 0° C. was slowly added 3M methylmagnesium bromide in ether (15.2 mL, 45.6 mmol) to give a yellow solution. After 1 hour, the reaction mixture was warmed to RT and was stirred for an additional 2.5 hours. The reaction was then quenched with MeOH (5 mL). The mixture was stirred for 15 minutes. Sodium borohydride (0.862, 22.8 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction was subsequently quenched with 1M HCl (5 mL). The mixture was stirred for 15 minutes, diluted with EtOAc, and washed with saturated aqueous NH4Cl (3×). The aqueous layer was concentrated to give the title compound as a brown solid, which was used without further purification.

Workup

  1. customat 0° C.
  2. customto give a yellow solution
  3. customThe reaction was then quenched with MeOH (5 mL)
  4. stirringThe mixture was stirred for 15 minutes
  5. stirringthe reaction mixture was stirred for 1 hour
  6. customThe reaction was subsequently quenched with 1M HCl (5 mL)
  7. stirringThe mixture was stirred for 15 minutes
  8. additiondiluted with EtOAc
  9. washwashed with saturated aqueous NH4Cl (3×)
  10. concentrationThe aqueous layer was concentrated

Sources & evidence

ORD record
ord-459045de32934c1b8e7f57b89c7e756b
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

Loading…