Dimethylformamide → 3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethyl-propionyl chloride

HRID 1948892Notes

Reaction equation

HRID 1948892 reaction equation
[C:1]([S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]([CH3:17])[CH3:16])[CH:13]=2)[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:7]=1[CH2:26][C:27]([CH3:32])([CH3:31])[C:28](O)=[O:29])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:36])=O.CN(C=O)C>C(Cl)Cl>[C:1]([S:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]([CH3:17])[CH3:16])[CH:13]=2)[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:7]=1[CH2:26][C:27]([CH3:31])([CH3:32])[C:28]([Cl:36])=[O:29])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 3651377MK 886

Product 1

HCID 866124193-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethyl-propionyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-[3-tert-butylsulfanyl-1-(4-chloro-benzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethyl-propionic acid (prepared according to the procedures described in U.S. Pat. No. 5,081,138 issued Jan. 14, 1992; 0.25 g, 0.53 mmol) suspended in CH2Cl2 (5 mL) was added oxalyl chloride (48 uL, 0.56 mmol) and catalytic DMF. The reaction was stirred at room temperature for 3 hours, and then concentrated to give I-1, which was used without further purification.

Workup

  1. concentrationconcentrated
  2. customto give I-1, which
  3. customwas used without further purification

Sources & evidence

ORD record
ord-32324f60fe924c4b8e232826eb2755a5
Source dataset
uspto-grants-2013_03
Patent number
US08399666B2

Reaction notes

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