Cesium carbonate → HCID 86685974, compound

HRID 2277680Notes

Reaction equation

HRID 2277680 reaction equation
N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[Cs+].[Cs+].Br[C:16]1[CH:17]=[C:18]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([Cl:32])[CH:28]=3)[C:23]2=[O:33])[CH:19]=[N:20][CH:21]=1.[CH2:34]([S:36]([NH2:39])(=[O:38])=[O:37])[CH3:35]>[Cu]I.O1CCOCC1>[Cl:32][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:33])[N:22]([C:18]1[CH:17]=[C:16]([NH:39][S:36]([CH2:34][CH3:35])(=[O:38])=[O:37])[CH:21]=[N:20][CH:19]=1)[CH2:31][CH2:30]2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 73702EthanesulfonamideHCID 145742L-ProlineHCID 86685975HCID 86685975, compound

Product 1

HCID 86685974HCID 86685974, compoundYield 20%

Reagents, catalysts & solvents 2

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

Procedure

CuI (1.9 mg, 0.01 mmol), L-proline (2.3 mg, 0.02 mmol) and Cs2CO3 (65 mg, 0.2 mmol) were added to a dioxane (3 mL) solution of 2-(5-bromo-pyridin-3-yl)-6-chloro-3,4-dihydro-2H-isoquinolin-1-one (example 7) (33.7 mg, 0.1 mmol) and ethanesulfonic acid amide (10.9 mg, 0.1 mmol). The resulting reaction mixture was subject to microwave reaction at 150° C. for 2.5 hours. The reaction mixture was filtered and concentrated in vacuo to give a crude product which was then purified by prep-HPLC to give title compound (7.3 mg, 20%) as a white solid. MS: 366.1 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. customreaction at 150° C. for 2.5 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated in vacuo
  5. customto give a crude product which
  6. customwas then purified by prep-HPLC

Sources & evidence

ORD record
ord-123a1e3e008945df82558a8a8e5ef033
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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