tert-Butyl mercaptan → HCID 58585855, compound

HRID 1297661Notes

Reaction equation

HRID 1297661 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].CCN(C(C)C)C(C)C.[CH3:24][C:25]([SH:28])([CH3:27])[CH3:26]>CN(C=O)C>[C:25]([S:28][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14])([CH3:27])([CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 81531DiisopropylethylamineHCID 224667694-Chloro-6-iodoquinoline-3-carbonitrile

Product 1

HCID 58585855HCID 58585855, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 4-chloro-6-iodo-quinoline-3-carbonitrile (example 14c, 1.0 g, 3.18 mmol) in anhydrous DMF (1 mL) and DIEA (1.67 mL, 9.54 mmol) was added 2-methyl-2-propanethiol (0.72 ul, 6.4 mmol). The mixture was stirred at room temperature for 4 h. The reaction was extracted with methylene chloride (2×100 mL). The combined organic layers were successively washed with water (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-50% ethyl acetate in hexanes in 30 min) afforded 4-tert-butylsulfanyl-6-iodo-quinoline-3-carbonitrile (0.57 g, 48%) as a white solid. LC-MS m/e 369 (MH+).

Workup

  1. extractionThe reaction was extracted with methylene chloride (2×100 mL)
  2. washThe combined organic layers were successively washed with water (3×50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2db4a1b2bbb4caeb6e498573f955e51
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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