1,2-Dichloroethane → 5-bromo-2-chloro-N-(4-chlorophenyl)nicotinamide

HRID 557339Notes

Reaction equation

HRID 557339 reaction equation
[CH2:1]([Cl:4])[CH2:2]Cl.C1C=[CH:7][C:8]2N(O)N=[N:11][C:9]=2[CH:10]=1.CCN(C(C)C)C(C)C.[Br:24][C:25]1[CH:26]=[N:27][C:28]([Cl:34])=[C:29]([CH:33]=1)[C:30]([OH:32])=O>C(Cl)Cl>[Br:24][C:25]1[CH:26]=[N:27][C:28]([Cl:34])=[C:29]([CH:33]=1)[C:30]([NH:11][C:9]1[CH:10]=[CH:2][C:1]([Cl:4])=[CH:7][CH:8]=1)=[O:32]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27633425-Bromo-2-chloronicotinic acid

Product 1

HCID 222492055-bromo-2-chloro-N-(4-chlorophenyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-chloroanaline (594 mg, 4.7 mmol, 1. eq.), EDC (1.62 g, 8.5 mmol, 2 eq.), HOBT (572 mg, 4.2 mmol, 1 eq.), and DIEA (1.1 ml, 6.3 mmol, 1.5 eq.) in CH2Cl2 (50 ml) was added 5-bromo-2-chloronicotinic acid from Step B (1.0 g, 4.2 mmol). The reaction was stirred at RT overnight. The solution was quenched with water and the organic layer was purified by chromatography (50% EtOAc in hexane) to afford a light-yellow compound. MS (ES+): 347.0, 349.0 (M+H)+; (ES−): 345.0, 347.0 (M−H)−.

Workup

  1. customThe solution was quenched with water
  2. customthe organic layer was purified by chromatography (50% EtOAc in hexane)
  3. customto afford a light-yellow compound

Sources & evidence

ORD record
ord-760ecb0b07054f4ba1d0afdfb9a7e123
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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