HCID 118036781, compound → HCID 118036623, compound

HRID 1778037Notes

Reaction equation

HRID 1778037 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[N:11]=[C:10]2[NH:12][CH:13]=[CH:14][C:9]2=[CH:8][CH:7]=1>[Ni].CCO>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[N:11]=[C:10]2[NH:12][CH2:13][CH2:14][C:9]2=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 118036781HCID 118036781, compound2×

Product 1

HCID 118036623HCID 118036623, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 6-(1,3-dioxolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (intermediate 292, 0.283 g, 1.443 mmol), and Raney nickel (0.140 g) in EtOH (30 ml) was stirred under a hydrogen atmosphere (5 bar) at 95° C. in an autoclave reactor. Additional Raney nickel (0.140 g) was added after 22 h. After 27 h, the reaction mixture was cooled to room temperature, poured onto a glass fiber filter, washed through with additional EtOH and concentrated to give the crude title compound as a brown oil. This was used withoug purification in the next step. (UPLC-MS 6) tR 0.38; ESI-MS 193.1 [M+H]+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. additionpoured onto a glass fiber
  3. filtrationfilter
  4. washwashed through with additional EtOH
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-425af0d4641f41849a6859798d8a4b80
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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