Benzylamine → HCID 57763148, compound

HRID 230757Notes

Reaction equation

HRID 230757 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[CH:18][C:11]=12>>[CH2:1]([N:8]1[C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[C:11]=2[CH:18]=[CH:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57763148HCID 57763148, compoundYield 55%

Conditions

Temperature
180 °C

Procedure

Benzylamine (1.8 mL, 16.4 mmol, 5 eq) was added to 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.50 g, 3.3 mmol, 1.0 eq; see, generally, Cheng, C.-C. et al. J. Physical Chem. 2003, 107, 1459-1471, incorporated by reference in its entirety) in a sealed tube and the reaction mixture was heated at 180° C. for 8 h. The reaction mixture was purified by loading it directly onto a C-18 YMC 30×500 mm reverse phase column (eluting 20-90% aqueous methanol with 0.1% TFA over a 30 minute gradient) and the appropriate fractions were isolated and concentrated in vacuo. The residue was neutralized with saturated aq. NaHCO3 solution and the mixture was extracted with CHCl3. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the product (0.40 g, 55%) as a solid. 1H NMR (DMSO-d6) δ 7.51-7.52 (m, 1H), 7.16-7.36 (m, 6H), 6.63-6.68 (m, 2H), 6.09 (s, 2H); MS(ESI+) m/z 224 (M+H)+. Calculated: 224.1188, found: 224.1178

Workup

  1. customThe reaction mixture was purified
  2. washeluting 20-90% aqueous methanol with 0.1% TFA over a 30 minute gradient) and the appropriate fractions
  3. customwere isolated
  4. concentrationconcentrated in vacuo
  5. extractionthe mixture was extracted with CHCl3
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdf4a5594df44ffb93eb964c21eb2dbc
Source dataset
uspto-grants-2009_07
Patent number
US07566784B2

Reaction notes

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