Cesium carbonate → HCID 10214984, compound

HRID 2121642Notes

Reaction equation

HRID 2121642 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[CH3:18][S:19]([NH2:22])(=[O:21])=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(Cl)Cl.[Cu]I>[CH3:12][C:8]1[CH:7]=[C:6]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]2[C:10](=[CH:11][C:2]([NH:22][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:3][CH:4]=2)[N:9]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 72879MethanesulfonamideHCID 113366637-Iodo-2-methyl-4-pyrrolidin-1-yl-quinoline

Product 1

HCID 10214984HCID 10214984, compoundYield 25.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

In a dried reaction flask flushed with argon a suspension of 169 mg (0.5 mmol) 7-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline and 57 mg (0.6 mmol) of methanesulfonamide, 325 mg (1 mmol) of cesium carbonate, 1.9 mg (0.01 mmol) copper (I) iodide in 1,4-dioxane was treated at RT with 5.7 mg (0.05 mmol) of trans-diaminocyclohexane and the mixture was heated at 110° C. (oil bath temperature) for 48 h under an argon atmosphere (for the gerneal method: Buchwald: J. Am. Chem. Soc., p7727, 2001). The reaction mixture was then cooled to RT, diluted with methylene chloride and filtered. The filtrate was concentrated in a vacuo, the residue was applied to silica gel column with CH2Cl2/MeOH/NH4OH (9:1:0.5) as eluent. Combination of the purified fractions and concentration in vacuo gave 29 mg (25.5%) of the desired N-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl)-methanesulfonamide which was re-crystallized from methylene chloride: light brown solid. ISP mass spectrum, m/e: 306.3 (M+1 calculated for C15H19IN3O2S: 306).

Workup

  1. customIn a dried reaction flask
  2. customflushed with argon
  3. temperatureThe reaction mixture was then cooled to RT
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in a vacuo
  6. concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-6668bfbc48c944569266ec5c345f464c
Source dataset
uspto-grants-2004_02
Patent number
US06696467B2

Reaction notes

Loading…