p-Chlorothiophenol → HCID 68006691, compound

HRID 2402091Notes

Reaction equation

HRID 2402091 reaction equation
Br[C:2]1[C:3]([C:28]#[N:29])=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=[O:27])[CH3:26])[CH:19]=2)[S:5][C:6]=1[C:7]1[N:11]=[CH:10][N:9]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[N:8]=1.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([SH:37])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu-]=O.CN(C=O)C>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37][C:2]2[C:3]([C:28]#[N:29])=[C:4]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=[O:27])[CH3:26])[CH:19]=3)[S:5][C:6]=2[C:7]2[N:11]=[CH:10][N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:8]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 66749558HCID 66749558, compound

Product 1

HCID 68006691HCID 68006691, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

N-(4-{4-bromo-3-cyano-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-2-thienyl}pyridin-2-yl)acetamide (0.2601 g, 0.5495 mmol), copper(I) oxide (0.1572 g, 1.099 mmol), 4-chlorobenzenethiol (0.3179 g, 2.198 mmol) and potassium carbonate (0.2278 g, 1.648 mmol) were added to a microwave vial followed by DMF (15.00 mL). The reaction was irradiated at 150° C. for 15 mins. The solid was filtered and washed with DCM. The solution was diluted with 80 ml water, and extracted with 100 ml DCM for two times. The organic layer was concentrated, and purified by column. The eluent was 50-100% ethyl acetate in hexane to yield a solid product (0.224 g, yield 76.0%) LCMS: (AA) ES+ 537, 539. 1H NMR (300 MHz, CDCl3) δ: 8.59 (s, 1H), 8.37 (d, 1H), 8.36 (s, 1H), 8.03 (s, 1H), 7.53 (d, 1H), 7.32 (d, 2H), 7.22 (d, 2H), 5.50-5.55 (dd, 1H), 4.02-4.08 (m, 1H), 3.68-3.78 (m, 1H), 2.25 (s, 3H), 2.10-2.18 (m, 1H), 2.00-2.07 (m, 2H), 1.66-1.80 (m, 3H).

Workup

  1. customThe reaction was irradiated at 150° C. for 15 mins
  2. filtrationThe solid was filtered
  3. washwashed with DCM
  4. additionThe solution was diluted with 80 ml water
  5. extractionextracted with 100 ml DCM for two times
  6. concentrationThe organic layer was concentrated
  7. custompurified by column

Sources & evidence

ORD record
ord-47e4b19cfa794ca8979b177381586b66
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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