Hydrogen Bromide → HCID 67204711, compound

HRID 1259369Notes

Reaction equation

HRID 1259369 reaction equation
Br.C([N:9]1[C:13]2=[C:14]([N+:29]([O-:31])=[O:30])[C:15]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=3[F:28])=[C:16]([CH3:19])[C:17](=[O:18])[N:12]2[CH2:11][CH2:10]1)C1C=CC=CC=1.C(OC(=O)C)C>C(O)(=O)C>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:15]2[C:14]([N+:29]([O-:31])=[O:30])=[C:13]3[NH:9][CH2:10][CH2:11][N:12]3[C:17](=[O:18])[C:16]=2[CH3:19])=[C:22]([F:28])[CH:23]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 67194489HCID 67194489, compound

Product 1

HCID 67204711HCID 67204711, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

HBr in acetic acid (20 mL) was added to 1-benzyl-7-(4-bromo-2-fluoro-phenylamino)-6-methyl-8-nitro-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (I-1f: 1.4 g) and the resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was partitioned between ice water and ethyl acetate. The organic layer was concentrated to afford the crude product. Purification by column chromatography on silica gel (65% ethylacetate in hexane) afforded 600 mg of the product (54.5% yield).

Workup

  1. customThe reaction mixture was partitioned between ice water and ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customto afford the crude product
  4. customPurification by column chromatography on silica gel (65% ethylacetate in hexane)

Sources & evidence

ORD record
ord-35faca57a04144a8884716455709c04b
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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