Methanol → 5-(3-Fluorophenyl)-1h-pyrrolo[2,3-b]pyridine

HRID 493148Notes

Reaction equation

HRID 493148 reaction equation
Cl[C:2]1[NH:17][C:5]2=[N:6][CH:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)[CH:9]=[C:4]2[CH:3]=1.CCN(CC)CC.CO>C1COCC1.[Pd]>[F:16][C:12]1[CH:11]=[C:10]([C:8]2[CH:9]=[C:4]3[CH:3]=[CH:2][NH:17][C:5]3=[N:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 469120842-Chloro-5-(3-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 103079645-(3-Fluorophenyl)-1h-pyrrolo[2,3-b]pyridineYield 115.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of chloride 6 (5.23 g, 21.3 mmol), 10% Pd/C (2.7 g), Et3N (3.6 mL, 25.8 mmol) in THF:MeOH=5:1 (180 mL) was stirred under H2 overnight. More 10% Pd/C (1.3 g) was added and stirring was continued for 3 h. Catalyst was removed by filtration and the solution was concentrated to dryness in vacuum. The residue was purified by SGC with CH2Cl2:AcOEt as eluent in gradient (up to 20% AcOEt) to afford 7 (5.23 g, 88%), greenish powder. 1H NMR (400 MHz, CDCl3) δ 6.59 (dd, J=3.5, 2.0 Hz, 1H), 7.04-7.10 (m, 1H), 7.33-7.37 (m, 1H), 7.40-7.48 (m, 3H), 8.14 (d, J=2.1 Hz, 1H), 8.57 (d, J=2.1 Hz, 1H), 9.91 (bs, 1H).

Workup

  1. customCatalyst was removed by filtration
  2. concentrationthe solution was concentrated to dryness in vacuum
  3. customThe residue was purified by SGC with CH2Cl2

Sources & evidence

ORD record
ord-3cd39778131b4638a46af63b23277997
Source dataset
uspto-grants-2009_05
Patent number
US07534800B2

Reaction notes

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