HCID 58362636, compound → HCID 58362463, compound

HRID 2361459Notes

Reaction equation

HRID 2361459 reaction equation
I[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:13]([C:15]1[CH:22]=[CH:21][C:18]([NH:19][CH3:20])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1)#[CH:14]>C(#N)C.[Cu]I>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:14]#[C:13][C:15]3[CH:22]=[CH:21][C:18]([NH:19][CH3:20])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=3)[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 2

HCID 58362636HCID 58362636, compoundHCID 58362708HCID 58362708, compound

Product 1

HCID 58362463HCID 58362463, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

A 5 mL microwave tube is charged with 2 (1 equiv), 4-ethynyl-N-methyl-2-nitroaniline (1 equiv) [Pd(PPh3)4] (0.05 equiv), CuI (0.05 equiv) and TEA (5 equiv) in ACN (5 vol). The suspension is irradiated in a Biotage Emrys Optimizer microwave reactor (250 W) at 100° C. for 5 min. After cooling to room temperature, the solvent is evaporated in vacuo. The residue is purified over silica gel using Hexanes:DCM (0-100%) as the eluent to afford the coupling product.

Workup

  1. customThe suspension is irradiated in a Biotage Emrys Optimizer microwave reactor (250 W) at 100° C. for 5 min
  2. customthe solvent is evaporated in vacuo
  3. customThe residue is purified over silica gel
  4. customDCM (0-100%) as the eluent to afford the coupling product

Sources & evidence

ORD record
ord-58ed168a92594f48bc8359403b0bd8ad
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

Loading…