Potassium Carbonate → 4-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-2-methyloxazole

HRID 79461Notes

Reaction equation

HRID 79461 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][C:22]1[N:23]=[C:24]([CH3:27])[O:25][CH:26]=1>CN(C=O)C.O>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:21][C:22]2[N:23]=[C:24]([CH3:27])[O:25][CH:26]=2)[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 441196044-(Bromomethyl)-2-methyloxazoleHCID 178526560HCID 178526560, compound

Product 1

HCID 672615694-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-2-methyloxazoleYield 43.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 3-bromo-4-nitro-1H-indazole (Preparation B; 500 mg, 2.07 mmol) and K2CO3 (1.14 g, 8.26 mmol) in anhydrous DMF (3 mL) was treated at ambient temperature, under a nitrogen atmosphere, with a solution of 4-(bromomethyl)-2-methyloxazole (727 mg, 2.07 mmol) (Org. Biom. Chem., 2003, 1, 4173-4208) in anhydrous DMF (2 mL). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with excess water and extracted multiple times with DCM and EtOAc. The combined extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product (0.5 g). The material was purified by preparative thin-layer chromatography (silica, 5% MeOH-DCM as eluent) to afford the product (304 mg) as a solid.

Workup

  1. extractionextracted multiple times with DCM and EtOAc
  2. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product (0.5 g)
  5. customThe material was purified by preparative thin-layer chromatography (silica, 5% MeOH-DCM as eluent)

Sources & evidence

ORD record
ord-fc7e86bbac614ccf843ec485b2fddcb2
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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