3-Fluoroaniline → HCID 69936228, compound

HRID 1623760Notes

Reaction equation

HRID 1623760 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[F:31][C:32]1[CH:33]=[C:34]([NH2:38])[CH:35]=[CH:36][CH:37]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([NH:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([F:31])[CH:33]=1)=[O:9]

Participants

5

Reactant 3

HCID 97423-FluoroanilineHCID 682631,1'-CarbonyldiimidazoleHCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Product 1

HCID 69936228HCID 69936228, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method C; 200 mg, 0.65 mmol) was added to a stirred suspension of CDI (106 mg, 0.65 mmol) in THF (6 ml) under nitrogen at 20° C. The reaction mixture was stirred at room temperature for 10 min and 3-fluorobenzenamine (72.4 mg, 0.65 mmol) was added dropwise. After refluxing for 14 h, the reaction mixture was concentrated to obtain crude product. The crude product was purified by silica gel chromatography eluting with hexane:ethyl acetate (10:1). The product was then purified by preparative HPLC (A: 0.05% trifluoroacetic acid/water B: dichloromethane) to yield the title compound. 73 mg.

Workup

  1. temperatureAfter refluxing for 14 h
  2. concentrationthe reaction mixture was concentrated
  3. customto obtain crude product
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with hexane:ethyl acetate (10:1)
  6. customThe product was then purified by preparative HPLC (A: 0.05% trifluoroacetic acid/water B

Sources & evidence

ORD record
ord-a20e6d7e310e4fd78505ff98c35d71e7
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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