Cesium carbonate → HCID 89600512, compound

HRID 2277707Notes

Reaction equation

HRID 2277707 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2.Br[C:13]1[C:21]2[CH2:20][CH2:19][CH:18]([NH2:22])[C:17]=2[CH:16]=[N:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+].N[C@H]1CCCC[C@@H]1N>O1CCOCC1.[Cu]I.O>[NH2:22][CH:18]1[C:17]2[CH:16]=[N:15][CH:14]=[C:13]([N:6]3[CH2:5][C:4]4[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=4)[C:7]3=[O:11])[C:21]=2[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 4793071,2-Diaminocyclohexane, (+)-HCID 197881085-Chloro-2,3-dihydro-1H-isoindol-1-oneHCID 717438934-Bromo-6,7-dihydro-5H-cyclopenta[C]pyridin-7-amine

Product 1

HCID 89600512HCID 89600512, compoundYield 80%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
150 °C

Procedure

In a 25 mL sealed tube, 5-chloro-2,3-dihydro-isoindol-1-one (801 mg, 4.8 mmol), 4-bromo-6,7-dihydro-5H-[2]pyrindin-7-ylamine (intermediate B-18 [C], 937 mg, 4.4 mmol), CuI (200 mg, 1.1 mmol), Cs2CO3 (3.0 g, 9.2 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.4 mL, 3.2 mmol) were dissolved in dioxane (16 mL). The resulting reaction mixture was heated at 150° C. for 3 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2×125 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient) to yield the title compound (1.02 g, 80%) as a light yellow solid. MS: 300.2 (M+H+).

Workup

  1. customIn a 25 mL sealed tube
  2. customThe resulting reaction mixture
  3. extractionextracted with EtOAc (2×125 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product which
  9. customwas purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient)

Sources & evidence

ORD record
ord-ae26fc67164b4fab9afa4e2de897b5e7
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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