Hydrogen Bromide → HCID 67192122, compound

HRID 1259374Notes

Reaction equation

HRID 1259374 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]([I: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)=O.[Na+]>C(O)(=O)C>[F:28][C:22]1[CH:23]=[C:24]([I:27])[CH:25]=[CH:26][C:21]=1[NH:20][C:15]1[C:14]([N+:29]([O-:31])=[O:30])=[C:13]2[NH:9][CH2:10][CH2:11][N:12]2[C:17](=[O:18])[C:16]=1[CH3:19]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 67191802HCID 67191802, compound

Product 1

HCID 67192122HCID 67192122, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

HBr in acetic acid (30 mL) was added to 1-benzyl-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-8-nitro-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (I-3b: 2.5 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 basified with NaHCO3 solution and partitioned between ice water and ethyl acetate. The organic layer was concentrated to afford the crude product. Purification by column chromatography on silica gel (60% ethylacetate in hexane) afforded 1.5 g of the product (75% yield).

Workup

  1. custompartitioned 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 (60% ethylacetate in hexane)

Sources & evidence

ORD record
ord-40dd3c3afb4a40108ca01e6996bc5db8
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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