Cesium carbonate → HCID 86686004, compound

HRID 2277713Notes

Reaction equation

HRID 2277713 reaction equation
Br[C:2]1[CH:3]=[C:4](NC)[CH:5]=[N:6][CH:7]=1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[NH:15][C:14]2([CH3:22])[CH3:21].C([O-])([O-])=O.[Cs+].[Cs+].[NH2:29][C@H:30]1CCCC[C@@H]1N>O1CCOCC1.[Cu]I.O>[NH2:29][CH2:30][C:4]1[CH:3]=[C:2]([N:15]2[C:14]([CH3:22])([CH3:21])[C:13]3[C:17](=[CH:18][CH:19]=[C:11]([Cl:10])[CH:12]=3)[C:16]2=[O:20])[CH:7]=[N:6][CH:5]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 4793071,2-Diaminocyclohexane, (+)-HCID 565998225-Bromo-N-methylpyridin-3-amineHCID 71743949HCID 71743949, compound

Product 1

HCID 86686004HCID 86686004, compoundYield 176.7%

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, a mixture of (5-bromo-pyridin-3-yl)-methylamine (281 mg, 1.5 mmol), 5-chloro-3,3-dimethyl-2,3-dihydro-isoindol-1-one (intermediate A-12, 196 mg, 1.0 mmol), CuI (38 mg, 0.2 mmol), Cs2CO3 (652 mg, 2.0 mmol) and (+)—(S,S)—1,2-diaminocyclohexane (68.4 mL, 0.6 mmol) were dissolved in dioxane (3 mL). The resulting reaction mixture was heated at 150° C. for 7 hours before it was poured into water (10 mL) and extracted with EtOAc (20 mL×2). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (320 mg, 100%). Without further purification, it was used directly in the next step. MS: 302.1 (M+H+).

Workup

  1. customIn a 25 mL sealed tube
  2. customThe resulting reaction mixture
  3. extractionextracted with EtOAc (20 mL×2)
  4. washThe combined organic layers were washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a045474e7d3647c88ce68d355953461a
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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