Triethylamine → HCID 57893547, compound

HRID 1821837Notes

Reaction equation

HRID 1821837 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[O:12])[NH:8][C:7]=12.C(N(CC)CC)C>CN(C)C=O.[Pd](Cl)Cl.[Pd]>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][NH:13][C:11]([C:9]1[NH:8][C:7]2=[CH:2][N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=1)=[O:12]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 57893471HCID 57893471, compound

Product 1

HCID 57893547HCID 57893547, compoundYield 28.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

7-Chloro-N-(2-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (Example 4) (0.06 g, 0.21 mmol) in N,N-dimethylformamide (4.2 mL) was warmed to 60° C. under a nitrogen atmosphere. To the stirring solution were added triethylamine (0.06 mL, 0.43 mmol) and palladium dichloride (spatula tip, catalytic amount), and the reaction mixture was placed under a hydrogen atmosphere. The formation of palladium black was observed within 15 min. After stirring at 60° C. for 2 h, the heating bath was removed and the reaction mixture was stirred at room temperature overnight under a hydrogen atmosphere. The crude reaction mixture was filtered through a pad of diatomaceous earth, and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with saturated NH4Cl and saturated NaCl, and dried over Na2SO4. Filtration and concentration provided N-(2-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (0.015 g, 25%) as an off-white solid: mp 230-236 C; 1H NMR (300 MHz, CD3OD) δ4.73 (2H, s), 7.20 (1H, s), 7.31-7.35 (1H, m), 7.46 (1H, d, J=7.9 Hz), 7.67 (1H, d, J=5.6 Hz), 7.79-7.83 (1H, m), 8.12 (1H, d, J=5.6 Hz), 8.50-8.52 (1H, m), 8.79 (1H, s); ESI MS m/z 253 [C14H12N4O+H]+; HPLC (Method A) 95.5% (AUC), tR=16.7 min.

Workup

  1. customthe heating bath was removed
  2. stirringthe reaction mixture was stirred at room temperature overnight under a hydrogen atmosphere
  3. customThe crude reaction mixture
  4. filtrationwas filtered through a pad of diatomaceous earth
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with saturated NH4Cl and saturated NaCl
  8. dry with materialdried over Na2SO4
  9. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-484fa302fb394adc99ff456c24f3c1c4
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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