Sodium cyanoborohydride → HCID 86689834, compound

HRID 2409021Notes

Reaction equation

HRID 2409021 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][C:6]([C:10](=O)[CH3:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.CN.[BH3-][C:17]#[N:18].[Na+]>CCO>[CH3:17][NH:18][CH:10]([C:6]1[N:5]=[C:4]2[CH:3]=[CH:2][NH:1][C:9]2=[CH:8][CH:7]=1)[CH3:11]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 86689828HCID 86689828, compound

Product 1

HCID 86689834HCID 86689834, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A microwave vial was charged with 1-(1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone (1.50 g, 9.36 mmol), methanamine hydrochloride (8.85 g, 131.1 mol), NaBH3CN (765.0 mg, 12.18 mmol), and anhydrous EtOH (31 mL) and stirred while irradiated in a microwave (300 Watts) at 130° C. for 2 min. The resulting solid was filtered and rinsed well with EtOH. The filtrate was concentrated in vacuo. The crude product was redissolved in EtOAc and twice washed with 10% aq. NaOH, water and brine. The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was triturated with DCM, and the insoluble solid was filtered through a pad of Celite®. The filtrate was concentrated in vacuo and dried under high vacuum to afford N-methyl-1-(1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine as a solid: 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 7.66 (d, J=8.4 Hz, 1H), 7.45 (d, J=3.3 Hz, 1H), 7.14 (d, J=8.4 Hz, 1H), 6.72 (d, J=3.3 Hz, 1H), 3.95 (q, J=6.7 Hz, 1H), 2.37 (s, 3H), 1.47 (d, J=6.7 Hz, 3H).

Workup

  1. customwhile irradiated in a microwave (300 Watts) at 130° C. for 2 min
  2. filtrationThe resulting solid was filtered
  3. washrinsed well with EtOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe crude product was redissolved in EtOAc
  6. washtwice washed with 10% aq. NaOH, water and brine
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was triturated with DCM
  11. filtrationthe insoluble solid was filtered through a pad of Celite®
  12. concentrationThe filtrate was concentrated in vacuo
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-9ca5e2b6eba540d7a9e639c2667574bd
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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