Trifluoroacetic acid → HCID 89704789, compound

HRID 928961Notes

Reaction equation

HRID 928961 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21].C1C(=O)N([I:29])C(=O)C1.FC(F)(F)C(O)=O>CN(C=O)C>[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:29])=[CH:17][C:16]=1[F:21]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 89704884HCID 89704884, compound

Product 1

HCID 89704789HCID 89704789, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-5-((2-fluorophenyl)amino)benzo[d]oxazole-6-carboxylic acid (7.22 g, 24.90 mmol) in DMF (50 mL) was added NIS (6.08 g, 26.37 mmol) followed by trifluoroacetic acid (3 mL). After stirring for 4 h at ambient temperature, the reaction was quenched with saturated NH4Cl (aq., 100 mL). The solution was extracted with ethyl acetate (150 mL×3). The combined organic extracts were washed with water (50 mL×3) and brine (100 mL) successively, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 3:1, v/v) and gave the desired product (brown solid, 6.339 g, 69% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.97 (s, 1H), 8.18 (s, 1H), 8.08 (s, 1H), 7.58 (dd, J=11.0, 1.7 Hz, 1H), 7.34 (d, J=8.5 Hz, 1H), 6.55 (m, 1H).

Workup

  1. customthe reaction was quenched with saturated NH4Cl (aq., 100 mL)
  2. extractionThe solution was extracted with ethyl acetate (150 mL×3)
  3. washThe combined organic extracts were washed with water (50 mL×3) and brine (100 mL) successively
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 3:1

Sources & evidence

ORD record
ord-6669ad93250e4d6aa4a72ad6ee105f23
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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