HCID 89924462, compound → HCID 89924349, compound

HRID 1500934Notes

Reaction equation

HRID 1500934 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]([CH2:18][OH:19])=[CH:5]2>C(Cl)Cl.O>[CH3:13][S:14]([O:19][CH2:18][C:6]1[N:7]([CH2:11][CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)(=[O:16])=[O:15]

Participants

4

Reactant 1

HCID 89924462HCID 89924462, compound

Product 1

HCID 89924349HCID 89924349, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-chloro-1-(3-methanesulfonyl-propyl)-1H-indol-2-yl]-methanol (0.60 g, 2.0 mmol) and TEA (0.60 g, 6 mmol) in 20 mL of DCM was added MsC1 (0.45 g, 4 mmol) in an ice bath. The reaction mixture was stirred at RT for 3 hours. The resulting mixture was diluted with 10 mL of water and then extracted with DCM (10 mL×3). The combined organic layers were dried over Na2SO4, and then concentrated in vacuo to afford the crude {5-chloro-1-[3-(methylsulfonyl)propyl]-1H-indol-2-yl}methyl methanesulfonate which was used in the next step without any purification.

Workup

  1. extractionextracted with DCM (10 mL×3)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59d2faba3e8a42a9a3451f3d16cc9251
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

Loading…