Dimethylformamide → HCID 178505514, compound

HRID 594928Notes

Reaction equation

HRID 594928 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:16][C:11]2=[CH:12][N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1.[OH-:17].[Na+].Cl[CH2:20][C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[C:33]([F:36])([F:35])[F:34])[CH:22]=1.CN([CH:40]=[O:41])C>>[F:34][C:33]([F:36])([F:35])[C:40]([O-:41])=[O:17].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[CH:15]=[CH:14][N:13]([CH2:20][C:21]3[O:25][N:24]=[C:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=4[C:33]([F:36])([F:34])[F:35])[CH:22]=3)[CH:12]=[C:11]2[NH+:16]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 468639965-Chloromethyl-3-(4-fluoro-2-trifluoromethyl-phenyl)-isoxazoleHCID 574382742-(2-Fluoro-phenyl)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 178505514HCID 178505514, compoundYield 81%

Procedure

To a solution of 2-(2-Fluoro-phenyl)-1H-pyrrolo[2,3-c]pyridine (50 mg, 0.244 mmole) in DMF (1 ml) was added 10% (w/v) aqueous NaOH (113 μl, 0.28 mmole) followed by a solution of 5-Chloromethyl-3-(4-fluoro-2-trifluoromethyl-phenyl)-isoxazole (79 mg, 0.28 mmole) in DMF (0.5 ml). The reaction mixture was stirred at room temperature for 12 hours. The crude reaction mixture was purified by reverse phase HPLC with mass directed collection. Obtained 109 mg (81%) of 2-(2-Fluoro-phenyl)-6-[3-(4-fluoro-2-trifluoromethyl-phenyl)-isoxazol-5-ylmethyl]-6H-pyrrolo[2,3-c]pyridinium trifluoroacetate.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by reverse phase HPLC with mass
  3. customcollection

Sources & evidence

ORD record
ord-6c385806003140f5a7735905b553d23d
Source dataset
uspto-grants-2016_01
Patent number
US09242983B2

Reaction notes

Loading…