Trifluoroacetic acid → HCID 89704789, compound

HRID 928952Notes

Reaction equation

HRID 928952 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 61.2%

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, 24.88 mmol) in DMF (50 mL) was added NIS (6.08 g, 26.37 mmol) followed by trifluoroacetic acid (1.0 mL). After stirring for 5 h at ambient temperature, the reaction was quenched by saturated NH4Cl (aq.). The solution was extracted with ethyl acetate (150 mL×3). The combined organic extracts were washed with water (100 mL) and brine (100 mL) successively, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 50:1, v/v) and gave the desired product (brown solid, 6.34 g, 61.2% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.97 (s, 1H), 8.58 (s, 1H), 8.18 (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 by saturated NH4Cl (aq.)
  2. extractionThe solution was extracted with ethyl acetate (150 mL×3)
  3. washThe combined organic extracts were washed with water (100 mL) 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 (CH2Cl2/MeOH, 50:1

Sources & evidence

ORD record
ord-b5923e90dd5141f788f342b9f2cb6672
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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