Water → HCID 11502325, compound

HRID 505927Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[N+:18]([O-:20])=[O:19])[NH:11][C:10]=2[CH3:21])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[N+:18]([O-:20])=[O:19])[N:11]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:10]=2[CH3:21])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

3-(4-Chlorophenylsulfanyl)-2-methyl-4-nitro-1H-indole (3.76 kg, 11.8 mol) and potassium carbonate (1.80 kg, 13.0 mol) were suspended in acetonitrile (32.7 kg). Water (0.53 kg) and a solution of ethyl bromoacetate (2.17 kg, 13.0 mol) in acetonitrile (5.75 kg) were added followed by an acetonitrile line rinse (2.97 kg). The mixture was heated at 50° C. for 6 hours then allowed to cool to 20° C. and held at this temperature overnight. Water (35.4 kg) was added to the reaction mixture and stirring continued for 30 minutes at 15° C. The solid product was collected by filtration, washed with acetonitrile (2.95 kg) then dried in a vacuum oven at 40° C. to afford [3-(4-chlorophenylsulfanyl)-2-methyl-4-nitro-1H-indol-1-yl]acetic acid, ethyl ester as a bright yellow solid, 4.33 kg (91%).

Workup

washrinse (2.97 kg)
temperatureto cool to 20° C.
customheld at this temperature overnight
additionWater (35.4 kg) was added to the reaction mixture
filtrationThe solid product was collected by filtration
washwashed with acetonitrile (2.95 kg)
customthen dried in a vacuum oven at 40° C.

Sources & evidence

ORD record: ord-2ec6444dbbc143fd9fe36e39eb337bd2
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781598B2

Reaction notes

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