Diisopropylethylamine → 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

HRID 2190519Notes

Reaction equation

HRID 2190519 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[I:9])[NH2:5].C(N(C(C)C)CC)(C)C.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][N:21]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([I:9])=[C:2]([CH3:1])[CH:3]=2)=[O:25])=[CH:22][N:21]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27342754-Iodo-3-methylanilineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamideYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-4-iodoaniline (660 mg 2.84 mmol), diisopropylethyl amine (1.2 mL 8.52 mmol) and a catalytic amount of DMAP in CH2Cl2 (15 mL) was treated with 6-chloronicotinoyl chloride (500 mg, 2.84 mmol). Upon completion of the reaction, as judged by TLC, the mixture was partitioned between CH2Cl2 and water. The EtOAc layer was dried over Na2SO4 filtered and concentrated. The solid residue was washed with hexanes and then was passed through a silica gel plug with 50% EtOAc in hexanes as the elution solvent to afford the product, 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide. (910 mg, Yield 86%).

Workup

  1. customUpon completion of the reaction
  2. customthe mixture was partitioned between CH2Cl2 and water
  3. dry with materialThe EtOAc layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe solid residue was washed with hexanes

Sources & evidence

ORD record
ord-170db9a435624e4ea45c95cc4881aedf
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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