Ethanethiol → HCID 10068483, compound

HRID 902035Notes

Reaction equation

HRID 902035 reaction equation
[CH2:1]([SH:3])[CH3:2].Cl[C:5]1[N:10]=[C:9]([C:11]2[C:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]3[N:12]=2)[CH:8]=[CH:7][CH:6]=1.[H-].[Na+]>CN(C=O)C.C(Cl)Cl>[CH2:1]([S:3][C:5]1[N:10]=[C:9]([C:11]2[C:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]3[N:12]=2)[CH:8]=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 59700605HCID 59700605, compound

Product 1

HCID 10068483HCID 10068483, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Add ethanethiol (0.71 mL, 0.96 mmol) to a solution of 4-[2-(6-chloro-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinoline (37 mg, 0.1 mmol) in DMF (2.5 mL) at 0° C. Add sodium hydride (38 mg, 0.96 mmol), stir the mixture at room temperature for 72 hours. Dilute the reaction mixture with methylene chloride (50 mL) and wash with water (2×50 mL), brine (1×50 mL). Dry the combined organic layers with sodium sulfate and concentrate. Purify the residue by flash column chromatography (SiO2, 50% ethyl acetate/hexanes) to give the title compound 35 mg (91%) as an off-white solid.

Workup

  1. washwash with water (2×50 mL), brine (1×50 mL)
  2. dry with materialDry the combined organic layers with sodium sulfate
  3. concentrationconcentrate
  4. customPurify the residue by flash column chromatography (SiO2, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6f5c77ea38f441c589ac450065875d41
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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