Dimethylformamide → HCID 178505515, compound

HRID 1023208Notes

Reaction equation

HRID 1023208 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:16][C:15]2[CH:14]=[CH:13][N:12]=[CH:11][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[NH+:16]=[C:15]2[C:10](=[CH:11][N:12]([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:13]=[CH:14]2)[CH:9]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 468639965-Chloromethyl-3-(4-fluoro-2-trifluoromethyl-phenyl)-isoxazoleHCID 57438275HCID 57438275, compound

Product 1

HCID 178505515HCID 178505515, compoundYield 86%

Procedure

To a solution of 2-(2-Fluoro-phenyl)-1H-pyrrolo[3,2-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 115 mg (86%) of 2-(2-Fluoro-phenyl)-5-[3-(4-fluoro-2-trifluoromethyl-phenyl)-isoxazol-5-ylmethyl]-5H-pyrrolo[3,2-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-c341aad5ce384c818581225cf7220bbf
Source dataset
uspto-grants-2014_05
Patent number
US08722677B2

Reaction notes

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