Water → HCID 22628315, compound

HRID 1386044Notes

Reaction equation

HRID 1386044 reaction equation
[OH-:1].[K+].[N:3]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[NH:18][C:19]4[C:24]([CH:25]=3)=[CH:23][N:22]=[CH:21][CH:20]=4)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.Br[C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[C:29]([O:37][CH3:38])[C:28]=1C.[OH2:40]>CS(C)=O>[C:30]([OH:40])(=[O:1])[C:31]([OH:33])=[O:32].[CH3:38][O:37][C:29]1[CH:28]=[C:27]([C:8]([N:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)=[O:1])[CH:36]=[CH:35][C:30]=1[CH2:31][N:18]1[C:19]2[C:24](=[CH:23][N:22]=[CH:21][CH:20]=2)[CH:25]=[C:17]1[C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 9861391HCID 9861391, compoundHCID 698169721427413-96-4

Product 1

HCID 22628315HCID 22628315, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Powdered KOH (730 mg, 13.0 mmol) was added to 25 mL of DMSO at ambient temperature. After 10 min, 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-5-azaindole (2.0 g, 6.5 mmol) was added. After 45 min, a solution of methyl 4-bromo-methyl-2-methoxybenzoate (1.69 g, 6.5 mmol) in 10 mL of DMSO was added dropwise via cannula. The resulting mixture was stirred overnight then poured into 100 mL of H2O. The aqueous solution was extracted with EtOAc (3×100 mL). The combined organic layers were dried over K2CO3, filtered and concentrated in vacuo. Purification of the crude residue by radial chromatography (SiO2; gradient of 0-2% MeOH/CHCl3, saturated with NH4OH) afforded 550 mg (1.13 mmol, 17%) of the title compound.

Workup

  1. waitAfter 45 min
  2. extractionThe aqueous solution was extracted with EtOAc (3×100 mL)
  3. dry with materialThe combined organic layers were dried over K2CO3
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude residue by radial chromatography (SiO2; gradient of 0-2% MeOH/CHCl3, saturated with NH4OH)

Sources & evidence

ORD record
ord-78199aef55ed403e886671e09c4f893d
Source dataset
uspto-grants-2001_07
Patent number
US06265416B1

Reaction notes

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