Tetrahydrofuran → HCID 59715673, compound

HRID 1673095Notes

Reaction equation

HRID 1673095 reaction equation
Cl[N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]=2[CH:4]=[CH:3]1.Cl[C:12]1[C:17](N)=[CH:16][CH:15]=[CH:14]N=1.[C:19](OCC)(=O)[CH3:20].O1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH2:26]([C:16]1[CH:17]=[CH:12][C:3]([CH2:4][C:5]2[N:10]=[CH:9][CH:8]=[C:7]3[CH:20]=[CH:19][NH:2][C:6]=23)=[CH:14][CH:15]=1)[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 805282-Chloro-3-pyridylamineHCID 67036713HCID 67036713, compound

Product 1

HCID 59715673HCID 59715673, compound

Procedure

The compound of Example B205 (800 μl, 0.3 mmol) was added to a solution of 1-chloropyrrolopyridine (19.4 mg, 0.127 mmol), which was synthesized from 2-chloro-3-aminopyridine according to the method of H07-165,708A, and dichloro(diphenylphosphinopropane)nickel (6.9 mg, 0.013 mmol) in tetrahydrofuran (1 ml) under ice-cooling, and the mixture was stirred while heating under reflux for 4 hours. After allowing the mixture to cool to room temperature, ethyl acetate was added thereto. The resulting mixture was washed with a saturated aqueous ammonium chloride solution and saturated brine, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (7.1 mg).

Workup

  1. temperaturecooling
  2. temperaturewhile heating
  3. temperatureunder reflux for 4 hours
  4. washThe resulting mixture was washed with a saturated aqueous ammonium chloride solution and saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8db0201e73434b9981bc11dbae47a76f
Source dataset
uspto-grants-2011_08
Patent number
US07999090B2

Reaction notes

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