Acetonitrile → HCID 56837600, compound

HRID 1466794Notes

Reaction equation

HRID 1466794 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.[H-].[Na+].Br.Br[CH2:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.C(#N)C>CN(C=O)C.O>[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]([C:11]([S:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:2])=[O:22])=[C:12]([CH3:21])[N:13]2[CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 127522194-(Bromomethyl)pyridine hbrHCID 66765016HCID 66765016, compound

Product 1

HCID 56837600HCID 56837600, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.050 g, 0.15 mmol) was dissolved in DMF (4 mL), cooled to ° C., and sodium hydride (60% dispersion in mineral oil, 0.015 g, 0.375 mmol) was added. After 15 minutes, 4-(bromomethyl)pyridine hydrobromide (0.057 g, 0.225 mmol) was added and the reaction stirred at room temperature for 70 minutes. The reaction was then heated to 50° C. for 2 hours then submitted to standard aqueous workup. Preparatory HPLC (10-100% ACN in H2O) afforded the title compound as a minor component.

Workup

  1. temperaturecooled
  2. temperatureThe reaction was then heated to 50° C. for 2 hours

Sources & evidence

ORD record
ord-940f9ed7b7b546fea622eaff5a478849
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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