Sodium cyanoborohydride → HCID 86689839, compound

HRID 2409024Notes

Reaction equation

HRID 2409024 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:7]2=[CH:8][N:9]=1)(=O)[CH3:2].[BH3-]C#[N:22].[Na+]>CO>[NH2:22][CH:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:7]2=[CH:8][N:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydride2×HCID 86689840HCID 86689840, compound

Product 1

HCID 86689839HCID 86689839, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sealed-cap vial was charged with tert-butyl 5-acetyl-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (225 mg, 0.86 mmol), NH4OAc ammonium acetate (666 mg, 8.6 mmol), NaBH3CN (71 mg, 1.1 mmol) and MeOH (7 mL). The reaction was stirred at RT for 24 h, after which additional NH4OAc (333 mg, 4.3 mmol) and NaBH3CN (27 mg, 0.43 mmol) were added. The reaction mixture was stirred for another 24 h then concentrated in vacuo. The residue was partitioned between 2N NaOH and EtOAc. The aqueous layer was thrice extracted with EtOAc. The organic extracts were combined and dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatography eluting with a mixture of EtOAc containing 1% TEA and MeOH to afford 95 mg (42%) of tert-butyl 5-(1-aminoethyl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate: MS (ESI) m/z: 262.2 [M+1]+.

Workup

  1. stirringThe reaction mixture was stirred for another 24 h
  2. concentrationthen concentrated in vacuo
  3. customThe residue was partitioned between 2N NaOH and EtOAc
  4. extractionThe aqueous layer was thrice extracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by SiO2 chromatography
  9. washeluting with a mixture of EtOAc containing 1% TEA and MeOH

Sources & evidence

ORD record
ord-3c7c4f32620145caaadacddf0bd3155a
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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