Ammonium formate → HCID 57893456, compound

HRID 1821854Notes

Reaction equation

HRID 1821854 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[OH:12])[NH:8][C:7]=12.C([O-])=O.[NH4+]>CO.[Pd]>[C:13]1([CH:11]([C:9]2[NH:8][C:7]3=[CH:2][N:3]=[CH:4][CH:5]=[C:6]3[CH:10]=2)[OH:12])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57893465HCID 57893465, compound

Product 1

HCID 57893456HCID 57893456, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanol (Example 26) (2.10 g, 8.12 mmol) and ammonium formate (3.07 g, 48.7 mmol) in methanol (28 mL) was added 10% Pd/C (0.21 g). The reaction mixture was refluxed for 1.5 h. TLC analysis showed the starting material was consumed. The reaction mixture was filtered through diatomaceous earth. The filtrate was concentrated to dryness. The crude mixture was dissolved in EtOAc and water. The aqueous layer was extracted with EtOAc (2×) and CH2Cl2. The combined organic extracts were dried over Na2SO4. After filtration and concentration, the crude material was purified by Biotage chromatography to provide phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (0.79 g, 43%) as an off-white solid: mp 178-180° C.; 1H NMR (300 MHz, CD3OD) δ5.99 (1H, s), 6.35 (1H, s), 7.20-7.49 (6H, m), 7.99 (1H, d, J=5.6 Hz), 8.58 (1H, s); ESI MS m/z 224 [C14H12N2O+H]+; HPLC (Method A) >99% (AUC) tR=14.5 min.

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 h
  2. customwas consumed
  3. filtrationThe reaction mixture was filtered through diatomaceous earth
  4. concentrationThe filtrate was concentrated to dryness
  5. dissolutionThe crude mixture was dissolved in EtOAc
  6. extractionThe aqueous layer was extracted with EtOAc (2×) and CH2Cl2
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationAfter filtration and concentration
  9. customthe crude material was purified by Biotage chromatography

Sources & evidence

ORD record
ord-3797b395a31c44da9c10e647eaf1f491
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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