HCID 55300171, compound → HCID 58362362, compound

HRID 2361457Notes

Reaction equation

HRID 2361457 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]([F:23])[CH:16]=1)#[CH:14]>C(#N)C.[Cu]I>[F:23][C:17]1[CH:16]=[C:15]([C:13]#[C:14][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH:22]=[CH:21][C:18]=1[NH:19][CH3:20]

Participants

5

Reactant 2

HCID 55300171HCID 55300171, compoundHCID 58362636HCID 58362636, compound

Product 1

HCID 58362362HCID 58362362, compoundYield 39.5%

Reagents, catalysts & solvents 2

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

Procedure

A 5 mL microwave tube was charged with 2 (0.2 g, 0.68 mmol), 7 (0.1 g, 0.68 mmol) [Pd(PPh3)4] (0.08 g, 0.034 mmol), CuI (0.02 g, 0.05 mmol) and TEA (0.28 mL, 2.04 mmol) in ACN (2.0 mL). The suspension was irradiated in a Biotage Emrys Optimizer microwave reactor (250 W) at 100° C. for 5 min. After cooling to room temperature the solvent was evaporated in vacuo. The residue was purified over silica gel using Hexanes:Dichloromethane (DCM) (0-100%) as the eluent to afford the coupling product 8 (0.084 g, 39%) as yellow solid. 1H NMR (400 MHz, CDCl3), δ: 2.92 (s, 3H), 3.87 (s, 3H), 6.64 (t, J=8.4 Hz, 1H), 7.11 (dd, J=12.0, 4.0 Hz, 1H), 7.22 (dd, J=10.4, 2 Hz, 1H), 7.27 (d, J=2.4, 1H), 7.33-7.35 (m, 1H), 7.96 (d, J=12 Hz, 1H); MS (ESI): 313.0 (M+H+).

Workup

  1. customThe suspension was irradiated in a Biotage Emrys Optimizer microwave reactor (250 W) at 100° C. for 5 min
  2. customwas evaporated in vacuo
  3. customThe residue was purified over silica gel

Sources & evidence

ORD record
ord-17d4d23e06de4009b6d54b96dc743ad2
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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