3-Fluoro-5-iodoaniline → 6-Chloro-N-(3-fluoro-5-iodo-phenyl)-nicotinamide

HRID 2190522Notes

Reaction equation

HRID 2190522 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([I:9])[CH:8]=1)[NH2:5].[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][N:12]=1.ClC1C=CC(C(NC2C=CC(I)=C(C)C=2)=O)=CN=1>>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:5][C:4]2[CH:6]=[C:7]([I:9])[CH:8]=[C:2]([F:1])[CH:3]=2)=[O:16])=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 27589863-Fluoro-5-iodoanilineHCID 27821656-Chloronicotinoyl ChlorideHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

Product 1

HCID 593179696-Chloro-N-(3-fluoro-5-iodo-phenyl)-nicotinamide

Procedure

6-Chloro-N-(3-fluoro-5-iodo-phenyl)-nicotinamide was prepared from 3-fluoro-5-iodo aniline and 6-chloronicotinoyl chloride following a procedure similar to the one described in the synthesis of 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide, above. The product was isolated after suspension in small volume of CH2Cl2, filtration and then a wash with hexanes. HRMS m/z calcd for C12H7N2OClFI [M+H]+: 376.9349. Found: 376.9348

Workup

  1. customThe product was isolated after suspension
  2. filtrationin small volume of CH2Cl2, filtration
  3. washa wash with hexanes

Sources & evidence

ORD record
ord-8e9cf803e2674684a5f981ee6724681d
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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