Pyridine → HCID 66891955, compound

HRID 1162007Notes

Reaction equation

HRID 1162007 reaction equation
[Br:1][C:2]1[C:10]2[O:9][C:8]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][C:6]=2[CH:5]=[C:4]([NH2:15])[CH:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[S:25](Cl)(=[O:27])=[O:26].N1C=CC=CC=1>ClCCl>[Br:1][C:2]1[C:10]2[O:9][C:8]([Si:11]([CH3:12])([CH3:14])[CH3:13])=[CH:7][C:6]=2[CH:5]=[C:4]([NH:15][S:25]([C:19]2[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=2[O:17][CH3:16])(=[O:27])=[O:26])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1451496-Methoxy-m-toluenesulfonyl chlorideHCID 595200137-Bromo-2-trimethylsilanyl-benzofuran-5-ylamine

Product 1

HCID 66891955HCID 66891955, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Coupling of the amine (4.5 g, 15.9 mmol) from Step 1 with 2-methoxy-5-methylphenylsulfonyl chloride (3.5 g, 15.9 mmol) in dichloromethane (200 mL) using pyridine as a base (3.2 mL, 40 mmol) required 2.5 hours at ambient temperature. Washing the resulting mixture with water, drying and concentration yielded 7.4 g (100%) of N-(7-bromo-2-trimethylsilanyl-benzofuran-5-yl)-2-methoxy-5-methyl-benzenesulfonamide as a dark orange solid.

Workup

  1. custom2.5 hours
  2. customat ambient temperature
  3. washWashing the resulting mixture with water
  4. customdrying
  5. concentrationconcentration

Sources & evidence

ORD record
ord-cbdc6dea8ad4483987320034baa35609
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

Loading…