3-Methoxyaniline → HCID 69936275, compound

HRID 1623758Notes

Reaction equation

HRID 1623758 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.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([NH2:39])[CH:36]=[CH:37][CH:38]=1>>[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:39][C:35]1[CH:36]=[CH:37][CH:38]=[C:33]([O:32][CH3:31])[CH:34]=1)=[O:9]

Participants

4

Reactant 3

HCID 108243-MethoxyanilineHCID 682631,1'-CarbonyldiimidazoleHCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Product 1

HCID 69936275HCID 69936275, compound

Procedure

Solid 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method B; 200 mg, 0.65 mmol) was added to a stirred suspension of CDI (106 mg, 0.65 mmol) in THE (6 ml) under nitrogen at 20° C. The reaction mixture was stirred at room temperature for 10 min and 3-methoxybenzenamine (80 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 crude product was added to a silica gel column and was eluted with DCM:hexane (2:1). The crude product was then added to a preparative HPLC column and was eluted with 0.05% trifluoroacetic acid, water/acetonitrile to yield the title compound. 110 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. additionThe crude product was added to a silica gel column
  7. washwas eluted with DCM:hexane (2:1)
  8. additionThe crude product was then added to a preparative HPLC column
  9. washwas eluted with 0.05% trifluoroacetic acid, water/acetonitrile

Sources & evidence

ORD record
ord-ae2d279f706b4a8e9b2dfaebd2e40947
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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