Ammonia → HCID 90093167, compound

HRID 1753036Notes

Reaction equation

HRID 1753036 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[N:12]([CH:19]([CH3:21])[CH3:20])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.[NH3:22]>>[NH2:22][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[N:12]([CH:19]([CH3:21])[CH3:20])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 90093975HCID 90093975, compound

Product 1

HCID 90093167HCID 90093167, compoundYield 60%

Conditions

Temperature
130 °C

Procedure

To a mixture of (5-bromopyridin-3-yl)(1-isopropyl-1H-pyrrolo[3,2-c]pyridin-3-yl)methanone (Preparation 37, 4.3 g, 12.5 mmol) in aqueous 880 ammonia (65 mL) was added CuSO4.5H2O (936 mg, 3.75 mmol) and the reaction was heated at 130° C. in an autoclave for 18 hours. The reaction was extracted into DCM and the organic layer collected, filtered, dried over sodium sulphate and concentrated in vacuo. The residue was purified through alumina eluting with 1-3% MeOH in DCM to afford the title compound as a white solid (2.1 g, 60%).

Workup

  1. extractionThe reaction was extracted into DCM
  2. customthe organic layer collected
  3. filtrationfiltered
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified through alumina eluting with 1-3% MeOH in DCM

Sources & evidence

ORD record
ord-f25ab87a3afb46f4bbab3388bbe8b766
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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