Pyridine → HCID 57387790, compound

HRID 881579Notes

Reaction equation

HRID 881579 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=1[C:10]([NH:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:11].[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:28]([NH:7][C:8]1[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=1[C:10]([NH:12][C:13]1[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:11])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 41390733HCID 41390733, compound

Product 1

HCID 57387790HCID 57387790, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (43 μL, 0.54 mmol) was added to a stirred solution of aniline 21 (50 mg, 0.18 mmol) in DCM (0.9 mL) at room temperature under nitrogen atmosphere. After 5 min, benzoylchloride 3 (22.5 μL, 0.198 mmol) was added and the reaction was stirred for 2 h before being diluted with DCM and washed with HCl (3×, aq, 1M), NaHCO3 (aq, sat), and brine. The organic phase was dried over Na2SO4, concentrated and purified by column chromatography (toluene:acetone 100:0→98:2) to give benzamide 23a in 62% yield (36 mg).

Workup

  1. washwashed with HCl (3×, aq, 1M), NaHCO3 (aq, sat), and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography (toluene:acetone 100:0→98:2)

Sources & evidence

ORD record
ord-d5cefb6eed35442b9d29a59308e280f0
Source dataset
uspto-grants-2015_03
Patent number
US08993622B2

Reaction notes

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