Sodium Hydroxide → 5-(2-Phenoxy-phenyl)-3-phenyl-1H-pyrrolo[2,3-b]pyridine

HRID 2114050Notes

Reaction equation

HRID 2114050 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:18]=[C:13]3[C:12]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[O:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:17]1[CH:18]=[C:13]2[C:12]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67051395HCID 67051395, compound

Product 1

HCID 598119395-(2-Phenoxy-phenyl)-3-phenyl-1H-pyrrolo[2,3-b]pyridineYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of azaindole 28 (1.16 g, 2.31 mmol) in EtOH (70 mL) was added a 10% sodium hydroxide solution (8.5 mL), and the mixture was heated at 105° C. After 1 h, the mixture was allowed to cool to r.t. and partitioned between chloroform and saturated brine. The aqueous layer was extracted with chloroform (3×), and the combined organic extracts dried (MgSO4), filtered and concentrated. The residue was purified by silicagel chromatography (gradient elution, hexanes to 5% EtOAc in dichloromethane) to afford a yellow solid which was washed with cold Et2O to furnish azaindole 29 (0.546 g, 65%) as a cream coloured solid. 1H NMR (400 MHz; CDCl3) δ6.95-6.98 (m, 2H), 7.04 (tt, J=7.4, 1.0 Hz, 1H), 7.11 (dd, J=8.1, 1.2 Hz, 1H), 7.25-7.31 (m, 4H), 7.35-7.41 (m, 3H), 7.54-7.57 (m, 4H), 8.41 (d, J=2.0 Hz, 1H), 8.58 (d, J=2.0 Hz, 1H), 10.78 (bs, 1H).

Workup

  1. temperatureto cool to r.t.
  2. custompartitioned between chloroform and saturated brine
  3. extractionThe aqueous layer was extracted with chloroform (3×)
  4. dry with materialthe combined organic extracts dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silicagel chromatography (gradient elution, hexanes to 5% EtOAc in dichloromethane)
  8. customto afford a yellow solid which
  9. washwas washed with cold Et2O

Sources & evidence

ORD record
ord-0e63b0a221034a919a5e0622538e5064
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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