Dichloromethane → HCID 69093586, compound

HRID 2174274Notes

Reaction equation

HRID 2174274 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:12]=[C:11]([C:13]3[N:14]=[CH:15][S:16][CH:17]=3)[NH:10][N:9]=2)[CH:3]=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>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:12]=[C:11]([C:13]3[N:14]=[CH:15][S:16][CH:17]=3)[N:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[N:9]=2)[CH:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:9]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[N:10]=[C:11]([C:13]3[N:14]=[CH:15][S:16][CH:17]=3)[N:12]=2)[CH:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 178419411HCID 178419411, compound

Product 2

HCID 69093586HCID 69093586, compoundHCID 69094013HCID 69094013, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring solution of 4-(3-(4-bromopyridin-2-yl)-1H-1,2,4-triazol-5-yl)thiazole (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 4-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole in 1% yield as a solid and 4-(5-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-3-yl)thiazole in 1% 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-c78d808fa6d943aab0c293a5b8b0cc9c
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

Loading…