Water → HCID 66863845, compound

HRID 1186708Notes

Reaction equation

HRID 1186708 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[C:25]([O:27][CH3:28])=[O:26])[C:19](O)=[O:20].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.O>CN(C=O)C>[I:15][C:16]1[CH:17]=[C:18]([C:19](=[O:20])[NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:22]=[CH:23][C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 75899Benzenamine, 2-phenoxy-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 154620563-Iodo-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 66863845HCID 66863845, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2-phenoxyaniline 99 (0.813 g, 4.39 mmol) and 3-iodo-4-(methoxycarbonyl)benzoic acid 100 (1.28 g, 4.18 mmol) in DMF (15 mL) was added BOP (1.942 g, 4.39 mmol) and TEA (1.166 mL, 8.36 mmol), the reaction mixture was stirred at room temperature for 1 h then poured into water. The desired product was extracted with ethyl acetate and the combined organic layers were washed with water, brine, dried over Na2SO4, filtered and solvent evaporated to provide methyl 2-iodo-4-(2-phenoxyphenylcarbamoyl)benzoate 101 (1.382 g, 70% yield) as a red foam after purification by flash chromatography (0 to 40% ethyl acetate in hexane).

Workup

  1. extractionThe desired product was extracted with ethyl acetate
  2. washthe combined organic layers were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customsolvent evaporated

Sources & evidence

ORD record
ord-1292d7c4adad45e1be03fb4866e64e93
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

Loading…