Pyridine → 4-(6-tert-Butyl-5-thiocyanato-2,3-dihydro-indole-1-sulfonyl)-benzonitrile

HRID 1859553Notes

Reaction equation

HRID 1859553 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][NH:11]2)=[CH:7][C:6]=1[S:14][C:15]#[N:16])([CH3:4])([CH3:3])[CH3:2].[C:17]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)#[N:18].N1C=CC=CC=1>C(Cl)Cl>[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][N:11]2[S:25]([C:22]2[CH:21]=[CH:20][C:19]([C:17]#[N:18])=[CH:24][CH:23]=2)(=[O:27])=[O:26])=[CH:7][C:6]=1[S:14][C:15]#[N:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 225729956-tert-butyl-5-thiocyanato-2,3-dihydro-1H-indole

Product 1

HCID 225730724-(6-tert-Butyl-5-thiocyanato-2,3-dihydro-indole-1-sulfonyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-tert-Butyl-5-thiocyanato-2,3-dihydro-1H-indole (prepared in Example JJ; 4.5 g, 19 mmol) was taken in CH2Cl2 (50 mL) and treated with 4-cyanophenylsulfonyl chloride (3.91 g, 19.4 mmol) and pyridine (5 mL). The reaction mixture was stirred overnight, quenched with saturated NaHCO3 solution, and diluted with EtOAc. The organic layer was separated, dried (MgSO4), and concentrated. The crude product was purified by flash chromatography (20%-75% EtOAc in hexanes as eluents). MS(APCI): 397 (M+).

Workup

  1. customquenched with saturated NaHCO3 solution
  2. additiondiluted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (20%-75% EtOAc in hexanes as eluents)

Sources & evidence

ORD record
ord-46eeb404b3694e09b91016268c49b9fd
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

Loading…