Ammonium Chloride → HCID 58528795, compound

HRID 1431011Notes

Reaction equation

HRID 1431011 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[C:14]([S:16][C:17]3[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=3)[C:13]([F:23])=[CH:12][C:11]=2[N+:24]([O-])=O)=[N:6][CH:7]=1.[NH4+].[Cl-]>[Fe].C(O)(C)C>[NH2:24][C:11]1[CH:12]=[C:13]([F:23])[C:14]([S:16][C:17]2[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=2)=[CH:15][C:10]=1[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:27]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58528917HCID 58528917, compound

Product 1

HCID 58528795HCID 58528795, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of N-(5-bromo-pyridin-2-yl)-4-fluoro-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-2-nitro-benzamide (1.42 g, 3.14 mmol). 325 mesh iron dust (7.1 g, 127 mmol), 6 mL of 4 M aqueous NH4Cl and 60 mL of isopropanol were mechanically stirred at 85° C. for 4 h, then slurried hot with Celite and filtered. The filtrate was diluted with EtOAc, washed with brine, dried (MgSO4) and evaporated. The residue obtained was triturated in boiling methanol. After cooling, the resulting solid was collected by filtration and dried under high vacuum to provide 692 mg (52%) of the title compound as a light-green solid. 1H NMR (500 MHz, DMSO-d6): δ 3.67 (s, 3H), 6.58 (d, 1H, J=12 Hz), 6.89 (s, 1H), 6.95 (br s, 2H), 7.26 (s, 1H). 7.99 (d, 1H, J=8 Hz), 8.03 (d, 1H, J=8 Hz), 8.04 (d, 1H, J=8 Hz), 8.50 (s, 1H). 10.86 (s, 1H); LCMS (m/z): 422/424 [C16H13BrFN5OS+H]+.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue obtained
  7. customwas triturated
  8. temperatureAfter cooling
  9. filtrationthe resulting solid was collected by filtration
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-6ab8948f3ce849e0bdebc97f422b5944
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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