p-Chlorothiophenol → HCID 86754257, compound

HRID 582651Notes

Reaction equation

HRID 582651 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:16]2[N:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([Cl:20])[C:4]=2[CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1>C(OCCO)C>[ClH:20].[F:1][C:2]1[CH:18]=[CH:17][C:16]2[NH+:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([S:28][C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 7815p-ChlorothiophenolHCID 67598476HCID 67598476, compound

Product 1

HCID 86754257HCID 86754257, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

To a solution of 2-fluoro-5-methyl-11-chloroquindoline from Example 24 (56 mg, 0.209 mmol) in 2-ethoxyethanol (5 mL) was added 4-chlorothiophenol (36 mg, 120 mol %). The reaction mixture was refluxed for 10 min, during which time the reaction mixture became orange and an orange precipitate formed. The reaction mixture was cooled to room temperature, filtered, and the solid was washed with ether and dried, affording 60 mg (73%) of the title compound, mp 254-256° C.; 1H NMR (DMSO-d6) δ 13.18 (s, 1H, NH), 9.00 (dd, 1H, J=4.4, J=5.2), 8.85 (d, 1H, J=8.4), 8.36 (d, 1H, J=8.0), 8.15 (t, 1H, J=7.2), 7.98 (d, 1H, J=8.0), 7.57 (t, 1H, J=7.2), 7.38-7.33 (m, 4H), 5.10 (s, 3H); 13C NMR (DMSO-d6) δ 161.64, 159.15, 146.27, 138.88, 138.15, 134.90, 132.65, 132.35, 132.07, 130.45, 129.66, 128.60, 126.98 122.77, 122.67, 121.67, 121.41, 114.55, 113.64, 109.83, 109.58, 41.29; MS (FAB, m/z) 393 (M+)

Workup

  1. temperatureThe reaction mixture was refluxed for 10 min, during which time the reaction mixture
  2. customan orange precipitate formed
  3. filtrationfiltered
  4. washthe solid was washed with ether
  5. customdried

Sources & evidence

ORD record
ord-052c361002064557b29e927809e9db4f
Source dataset
uspto-grants-1999_07
Patent number
US05925647

Reaction notes

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