4-Nitrophenol → HCID 58733604, compound

HRID 855774Notes

Reaction equation

HRID 855774 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[C:5]([C:12]#[N:13])=[CH:4][C:3]=1[F:14].[N+:15]([C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1)([O-:17])=[O:16].C(N=C=NC(C)C)(C)C>C(Cl)Cl>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([O:10][C:9](=[O:11])[CH2:8][C:6]2[C:5]([C:12]#[N:13])=[CH:4][C:3]([F:14])=[C:2]([Cl:1])[N:7]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 12734DiisopropylcarbodiimideHCID 58936500HCID 58936500, compound

Product 1

HCID 58733604HCID 58733604, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A homogeneous brown solution of (6-chloro-3-cyano-5-fluoro-pyridin-2-yl)-acetic acid (2.37 g, 11.0 mmol), as prepared in the previous step, 4-nitrophenol (1.84 g, 13.2 mmol), and DCM (11 mL) was stirred under argon at 0° C. while 1,3-diisopropylcarbodiimide (DIC) (1.90 mL, 12.1 mmol) was added dropwise with stirring over 3 min. The ice bath was immediately removed following completion of the DIC addition, and the brown mixture with yellowish precipitate was stirred at rt for 1 h 40 min. The crude reaction was then directly loaded onto a flash silica column and eluted with 96:4 toluene/CH3CN to afford the title compound as a translucent pale yellow oil (3.11 g, 84%). 1H-NMR (300 MHz, CDCl3) δ 8.29 (m, 2H), 7.80 (d, 1H), 7.35 (m, 2H), 4.35 (d, 0.7 Hz, 2H).

Workup

  1. additionwas added dropwise
  2. customThe ice bath was immediately removed
  3. additioncompletion of the DIC addition
  4. stirringthe brown mixture with yellowish precipitate was stirred at rt for 1 h 40 min
  5. customThe crude reaction
  6. washeluted with 96:4 toluene/CH3CN

Sources & evidence

ORD record
ord-f144c3eb528d47a8a71e3605f1e2adfa
Source dataset
uspto-grants-2007_08
Patent number
US07262210B2

Reaction notes

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