Pyridine → HCID 22050151, compound

HRID 1831963Notes

Reaction equation

HRID 1831963 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[C:11]([Br:26])[C:10]2=[O:27])[CH:6]=[CH:7][CH:8]=1.N1C=CC=CC=1.Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=1)=[O:36]>ClCCl>[Br:26][C:11]1[C:10](=[O:27])[N:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[CH2:2][NH:1][C:35](=[O:36])[O:37][C:38]2[CH:39]=[CH:40][C:41]([N+:44]([O-:46])=[O:45])=[CH:42][CH:43]=2)[C:14]([CH3:15])=[CH:13][C:12]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformate2×HCID 22051179HCID 22051179, compound

Product 1

HCID 22050151HCID 22050151, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1-[3-(aminomethyl)phenyl]-3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one (1.08 g, 2.48 mmol) was suspended in dichloromethane (7.5 mL). Pyridine was added (0.222 mL, 2.74 mmol). After stirring for 10 minutes at room temperature, a stock solution of 4-nitrophenyl chloroformate (5.0 mL, 0.50 M) in dichloromethane was added dropwise. After stirring for 4.5 hours at room temperature, a stock solution of 4-nitrophenyl chloroformate (2.5 mL, 0.50 M) in dichloromethane was again added dropwise and stirring continued at room temperature overnight. The reaction mixture was concentrated and subjected to chromatography (silica gel, ethyl acetate with 10% methanol/hexanes) afforded a yellow solid (0.85 g, 57%).

Workup

  1. stirringAfter stirring for 4.5 hours at room temperature
  2. stirringstirring
  3. waitcontinued at room temperature overnight
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-6400906b4f3645299319f2b8265c33b7
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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