Methyl vinyl sulfone → HCID 86671273, compound

HRID 2200066Notes

Reaction equation

HRID 2200066 reaction equation
[CH3:1][S:2]([CH:5]=[CH2:6])(=[O:4])=[O:3].[Cl:7][C:8]1[CH:17]=[CH:16][C:15]2[CH2:14][NH:13][CH2:12][CH2:11][C:10]=2[N:9]=1>CCO>[Cl:7][C:8]1[CH:17]=[CH:16][C:15]2[CH2:14][N:13]([CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:12][CH2:11][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 184491662-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 1

HCID 86671273HCID 86671273, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Methylsulfonylethene (commercially available from Sigma-Aldrich, St. Louis, Mo.) (142 mg, 1.33 mmol) was added dropwise to a solution of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine (150 mg, 0.89 mmol, commercially available from D-L Chiral Chemicals, ST-0143) in EtOH (10 mL). The reaction mixture was stirred at 60° C. for 2 hours, and then concentrated and purified by flash chromatography on silica gel eluting with 0% to 5% MeOH in DCM to give 2-chloro-6-(2-(methylsulfonyl)ethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine (220 mg, 90% yield). 1H NMR (400 MHz, CD3OD) δ ppm 2.91-3.11 (9H, m) 3.43 (2H, t, J=6.65 Hz) 3.73-3.77 (2H, m) 7.26 (1H, d, J=8.22 Hz) 7.56 (1H, d, J=8.02 Hz) ppm; LC/MS m/z: 275 (M+1).

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography on silica gel eluting with 0% to 5% MeOH in DCM

Sources & evidence

ORD record
ord-13d6fd7935714b958152b0487b78ec0a
Source dataset
uspto-grants-2016_06
Patent number
US09359355B2

Reaction notes

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