Diethyl Ether → 1-(5-(1-Aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-4-methylpiperidin-4-ol

HRID 75302Notes

Reaction equation

HRID 75302 reaction equation
[OH:1][C:2]1([CH3:20])[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]3[N:18]([CH3:19])[CH:17]=[CH:16][C:11]3=[N:12][C:13]=2[C:14]#[N:15])[CH2:4][CH2:3]1.[CH3:21][Mg]Br.CCOCC.[BH4-].[Na+]>C1COCC1>[NH2:15][CH:14]([C:13]1[N:12]=[C:11]2[CH:16]=[CH:17][N:18]([CH3:19])[C:10]2=[CH:9][C:8]=1[N:5]1[CH2:6][CH2:7][C:2]([CH3:20])([OH:1])[CH2:3][CH2:4]1)[CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 867080016-(4-hydroxy-4-methylpiperidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 867080001-(5-(1-Aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-4-methylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(4-hydroxy-4-methylpiperidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (245 mg, 0.906 mmol) in THF (5 mL) at 0° C. was slowly added 3M methylmagnesium bromide in ether (1.21 mL, 3.63 mmol). The resulting yellow solution was stirred at 0° C. for 2.5 hours. The reaction was quenched with MeOH (5 mL) and stirred for 15 minutes at RT. Sodium borohydride (68.6 mg, 1.81 mmol) was added. The reaction was stirred for 1 hour, quenched with 1M HCl (5 mL), and then stirred for an additional 15 minutes. The mixture was subsequently diluted with EtOAc and washed with saturated aqueous NaHCO3 (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give the title compound, which was used without further purification. ESI-MS m/z [M+H]+ calc'd for C16H24N4, 289; found 289.

Workup

  1. customat 0° C.
  2. customThe reaction was quenched with MeOH (5 mL)
  3. stirringstirred for 15 minutes at RT
  4. stirringThe reaction was stirred for 1 hour
  5. customquenched with 1M HCl (5 mL)
  6. stirringstirred for an additional 15 minutes
  7. additionThe mixture was subsequently diluted with EtOAc
  8. washwashed with saturated aqueous NaHCO3 (3×)
  9. dry with materialThe combined organic layers were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72b9dea6ea1c429bb7dfd511c8b7aadd
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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