Water → HCID 86685988, compound

HRID 2277691Notes

Reaction equation

HRID 2277691 reaction equation
C[O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=1.[Cl:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[NH:19][CH2:18][CH2:17]2.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.[Cu]I>[Cl:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([C:9]1[CH:10]=[C:5]([CH2:4][C:3]([OH:2])=[O:12])[CH:6]=[N:7][CH:8]=1)[CH2:18][CH2:17]2

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 193756376-Chloro-3,4-dihydroisoquinolin-1(2H)-oneHCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetate

Product 1

HCID 86685988HCID 86685988, compoundYield 72.6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

(5-Bromo-pyridin-3-yl)-acetic acid methyl ester (230 mg, 1.0 mmol), 6-chloro-3,4-dihydro-2H-isoquinolin-1-one (intermediate A-2) (182 mg, 1.0 mmol), CuI (40 mg, 0.21 mmol), Cs2CO3 (650 mg, 2.0 mmol) and (+)-(1S,1S)-1,2-diaminocyclohexane (0.1 mL, 0.8 mmol) were dissolved in dioxane (4.0 ml) and the resulting reaction mixture was heated at 150° C. for 2 hours before it was poured into H2O (20 mL) and extracted with EtOAc (2×100 mL). The combined organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (230 mg, 72.5%) as light brown oil. MS: 317.1 (M+H+).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layer was washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1cbaef82c0241bb8dbff004bf378827
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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