Trifluoroacetic acid → HCID 89705458, compound

HRID 929052Notes

Reaction equation

HRID 929052 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22].C1C(=O)N([I:30])C(=O)C1.FC(F)(F)C(O)=O>CN(C=O)C>[F:1][C:2]1[C:7]2[N:8]=[N:9][S:10][C:6]=2[CH:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:30])=[CH:18][C:17]=1[F:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 89705382Methyl 4-fluoro-5-((2-fluorophenyl)amino)benzo[d][1, 2,3]thiadiazole-6-carboxylate

Product 1

HCID 89705458HCID 89705458, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-fluoro-5-((2-fluorophenyl)amino)benzo[d][1,2,3]thiadiazole-6-carboxylate (1.53 g, 4.77 mmol) in DMF (10 mL) was added NIS (1.18 g, 5.24 mmol) followed by trifluoroacetic acid (0.5 mL). After stirring for 4 h at ambient temperature, the reaction was quenched with saturated NH4Cl (aq.). The solution was extracted with ethyl acetate (30 mL×3). The combined organic extracts were washed with water (30 mL×3) and brine (30 mL) successively, dried over Na2SO4 and concentrated in vacuo to give the desired product (yellow solid, 1.90 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.49 (s, 1H), 7.38 (d, J=10.3 Hz, 1H), 7.29 (d, J=8.6 Hz, 1H), 6.64 (dd, J=14.3, 8.3 Hz, 1H), 3.94 (s, 3H).

Workup

  1. customthe reaction was quenched with saturated NH4Cl (aq.)
  2. extractionThe solution was extracted with ethyl acetate (30 mL×3)
  3. washThe combined organic extracts were washed with water (30 mL×3) and brine (30 mL) successively
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69a452d4f6fb43809d0540a13a686904
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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