Water → HCID 59426190, compound

HRID 252584Notes

Reaction equation

HRID 252584 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:13]([CH2:24][CH3:25])[C:14]3[C:19]([C:20]=2[C:21]#[N:22])=[CH:18][CH:17]=[C:16]([OH:23])[CH:15]=3)[CH:7]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:34][CH2:35][CH2:36]Cl.O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:13]([CH2:24][CH3:25])[C:14]3[C:19]([C:20]=2[C:21]#[N:22])=[CH:18][CH:17]=[C:16]([O:23][CH2:34][CH2:35][CH2:36][N:13]2[CH2:14][CH2:19][CH2:20][CH2:12]2)[CH:15]=3)[CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 59426403HCID 59426403, compound

Product 1

HCID 59426190HCID 59426190, compoundYield 164.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of [3-(3-cyano-1-ethyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid ethyl ester (1.2 g, 2.91 mmol) in DMF (10 mL) is added K2CO3 (538 mg, 3.9 mmol) and 3-bromo-1-chloropropane (383 uL, 3.9 mmol) and the reaction is stirred for overnight at 50° C. The reaction mixture is then poured into cold water and the precipitate is collected by filtration and washed with hexane and dried in vacuo to afford 1.1 g, 89% of the desired product.

Workup

  1. filtrationthe precipitate is collected by filtration
  2. washwashed with hexane
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ca2864119a434f66b711dc58b1f89da3
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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