Ammonium formate → HCID 57893551, compound

HRID 1821858Notes

Reaction equation

HRID 1821858 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])[NH:15][C:12]2=[CH:13][N:14]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO.C(O)C>[NH2:8][C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([CH:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[OH:19])[NH:15][C:12]2=[CH:13][N:14]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 57893557HCID 57893557, compound

Product 1

HCID 57893551HCID 57893551, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of [5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone (Example 55) (674 mg, 1.61 mmol), ammonium formate (2.04 g, 32.3 mmol) and 10% palladium on carbon (350 mg, 50% by wt.) in methanol (40.2 mL) and ethanol (40.2 mL) was heated under reflux for 1 h. The reaction mixture was filtered through diatomaceous earth to remove the catalyst. After concentration to dryness, the residue was treated with a small amount of methanol (ca. 3 mL) and a precipitate formed. The solid was filtered, rinsed with a small amount of methanol, and collected. Additional material was obtained from Biotage chromatography of the filtrate. This provided (5-amino-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanol (119 mg, 32%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ5.81 (1H, s), 5.94 (1H, s), 6.44 (1H, s), 7.27-7.53 (5H, m), 8.06 (1H, s), 8.20 (1H, s), 10.9 (1H, br s); ESI MS m/z 240 [C14H13N3O+H]+; HPLC (Method A) 89.0% (AUC), tR=14.0 min.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. filtrationThe reaction mixture was filtered through diatomaceous earth
  4. customto remove the catalyst
  5. concentrationAfter concentration to dryness
  6. additionthe residue was treated with a small amount of methanol (ca. 3 mL)
  7. customa precipitate formed
  8. filtrationThe solid was filtered
  9. washrinsed with a small amount of methanol
  10. customcollected

Sources & evidence

ORD record
ord-b6a9317c6d1e4f5e9a459914304270cb
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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