Dimethylformamide → HCID 69093847, compound

HRID 2174273Notes

Reaction equation

HRID 2174273 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:17]=[CH:16][O:15][N:14]=2)[NH:10][N:9]=1.[H-].[Na+].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28].C(Cl)Cl.C[N:33](C=O)C>[Cl-].[Na+].O>[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][N:10]1[C:11]([C:13]2[CH:17]=[CH:16][O:15][N:14]=2)=[N:12][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)=[N:9]1.[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][N:10]1[C:11]([C:13]2[CH:17]=[CH:16][O:15][N:14]=2)=[N:12][C:8]([C:3]2[N:2]=[CH:7][CH:6]=[CH:5][N:33]=2)=[N:9]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 178478001HCID 178478001, compound

Product 2

HCID 69093847HCID 69093847, compoundHCID 69280931HCID 69280931, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring solution of 3-(3-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)isoxazole hydrochloride (1 eq) in DMF was added sodium hydride (2.1 eq). After 10 minutes, 1-(bromomethyl)-2-fluorobenzene (1.1 eq) was added and the reaction was stirred overnight at room temperature. Brine was used to quench the reaction. Methylene chloride was used to extract the aqueous layer. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. SiO2 chromatography yielded 3-(1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)isoxazole in 13.5% yield as a solid and 3-(1-(2-fluorobenzyl)-3-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)isoxazole in 15.7% yield as a solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionto extract the aqueous layer
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f77e010240574980af5787a8ba8aafa6
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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