Potassium Carbonate → HCID 67976106, compound

HRID 706740Notes

Reaction equation

HRID 706740 reaction equation
[I: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[S:26][C:25]([CH3:27])=[N:24][CH:23]=1>CN(C=O)C.O.CCOC(C)=O>[I: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[S:26][C:25]([CH3:27])=[N:24][CH:23]=2)[N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 552507865-(Bromomethyl)-2-methyl-1,3-thiazoleHCID 178526562HCID 178526562, compound

Product 1

HCID 67976106HCID 67976106, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-iodo-4-nitro-1H-indazole (441 mg, 1.53 mmol) in anhydrous DMF (3 mL) were added potassium carbonate (422 mg, 3.05 mmol), and 5-(bromomethyl)-2-methylthiazole (440 mg, 2.30 mmol) at ambient temperature and under a nitrogen atmosphere. The resulting mixture was stirred at ambient temperature overnight (about 18 hours). The reaction mixture was diluted with water (10 mL) and EtOAc (20 mL). The phases were separated and the aqueous phase was extracted with EtOAc (2×25 mL). The combined organic extracts were concentrated, and the residue subjected to flash liquid chromatography on silica with Hexanes:EtOAc (10:1) as the eluent to afford the desired product (611 mg).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×25 mL)
  3. concentrationThe combined organic extracts were concentrated

Sources & evidence

ORD record
ord-580bce65506544febaeb4232d83d5177
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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