Cesium carbonate → HCID 86685941, compound

HRID 2277618Notes

Reaction equation

HRID 2277618 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:13])([CH3:12])[NH:9][C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1.Br[C:15]1[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[N:19][CH:20]=1.[C@H]1(N)CCCC[C@@H]1N.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.[Cu]I.O>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:13])([CH3:12])[N:9]([C:15]3[CH:20]=[N:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=3)[C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 4793071,2-Diaminocyclohexane, (+)-HCID 2784733(5-Bromo-3-pyridinyl)methanolHCID 717438192-Chloro-7,7-dimethyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

Product 1

HCID 86685941HCID 86685941, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-7,7-dimethyl-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one (intermediate A-16 [G], 39.2 mg, 0.2 mmol), (5-bromo-pyridin-3-yl)-methanol (example 3 [A], 74.8 mg, 0.4 mmol), CuI (3.8 mg, 0.02 mmol), (1S,2S)-cyclohexane-1,2-diamine (4.5 mg, 0.04 mmol) and Cs2CO3 (130 mg, 0.4 mmol) were dissolved in dioxane (5 mL). The reaction mixture was subjected to microwave reaction at 140° C. for 1 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2×25 mL). The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (55.7 mg, 92%) as solid. MS: 304.1 (M+H+).

Workup

  1. customreaction at 140° C. for 1 hours before it
  2. extractionextracted with EtOAc (2×25 mL)
  3. washThe organic layer was washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f8ff79e519f46f6b245f37526ba302a
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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