Dimethylformamide → HCID 178505514, compound

HRID 1023207Notes

Reaction equation

HRID 1023207 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-a21b4833ad694661919841c2c88c0b67
Source dataset
uspto-grants-2014_05
Patent number
US08722677B2

Reaction notes

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