Diisopropylethylamine → HCID 67070067, compound

HRID 2390816Notes

Reaction equation

HRID 2390816 reaction equation
Br[C:2]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([Br:14])[C:3]=1[C:4]#[N:5].[C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=1)#[CH:16].CCN(C(C)C)C(C)C>>[Br:14][C:6]1[C:3]([C:4]#[N:5])=[C:2]([C:16]#[C:15][C:17]2[CH:18]=[CH:19][C:20]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])=[CH:21][CH:22]=2)[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 3749345N-(4-Ethynylphenyl)methanesulfonamideHCID 59156597HCID 59156597, compound

Product 1

HCID 67070067HCID 67070067, compoundYield 35.8%

Conditions

Temperature
80 °C

Procedure

step 2—A mixture of 92 (0.750 g, 1.90 mmol), Cu(I) (0.027 g, 0.09 mmol), Pd(II)(PPh3)2Cl2 (0.203 g, 0.19 mmol), 80 (0.748 g, 2.85 mmol) and DIPEA (5 mL mL) under an argon atmosphere was heated overnight at 80° C. The reaction was cooled to RT then concentrated. The crude residue was purified by SiO2 chromatography eluting with 40% EtOAc/hexanes to afford 0.293 g (24%) of N-[4-(3-bromo-5-tert-butyl-2-cyano-phenylethynyl)-phenyl]-methanesulfonamide (94) as a light brown solid.

Workup

  1. temperatureThe reaction was cooled to RT
  2. concentrationthen concentrated
  3. customThe crude residue was purified by SiO2 chromatography
  4. washeluting with 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-13973eee215a4b25b1ad88758924e4ad
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

Loading…