Hydrogen Bromide → HCID 178523849, compound

HRID 509440Notes

Reaction equation

HRID 509440 reaction equation
Br.[F:2][C:3]1[CH:4]=[C:5]([C@@H:14]([C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][N:30]=2)[NH:15][C:16](=[O:28])[C:17]2[CH:22]=[C:21]([O:23]C)[C:20]([N+:25]([O-:27])=[O:26])=[CH:19][N:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:13])([F:12])[F:11].CCOC(C)=O>CC(O)=O>[F:2][C:3]1[CH:4]=[C:5]([C@@H:14]([C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][N:30]=2)[NH:15][C:16](=[O:28])[C:17]2[CH:22]=[C:21]([OH:23])[C:20]([N+:25]([O-:27])=[O:26])=[CH:19][N:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 71144214HCID 71144214, compound

Product 1

HCID 178523849HCID 178523849, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 30% HBr in AcOH (10 mL, Spectrochem, India) was added (S)—N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-4-methoxy-5-nitropicolinamide (1 g, 0.002 mol), and the resulting reaction mixture was stirred for 12 h at 90° C. The reaction progress was monitored by TLC (50% EtOAc in petroleum ether). After completion of the reaction, the reaction mixture was concentrated and neutralized with sat'd NaHCO3 solution (pH˜7-7.5) and the aqueous solution was extracted with EtOAc (3×10 mL). The combined organic layers were dried over anhydrous sodium sulfate, and concentrated to afford the title compound as a pale yellow solid. 1H NMR (DMSO-d6) δ: 9.84 (d, J=7.5 Hz, 1H), 8.77 (s, 1H), 8.53 (d, J=4.5 Hz, 1H), 7.83-7.70 (m, 1H), 7.57-7.49 (m, 3H), 7.38-7.31 (m, 2H), 6.56 (d, J=7.5 Hz, 1H). MS (ESI, positive ion) m/z: 471.4 (M+H).

Workup

  1. customthe resulting reaction mixture
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated
  4. extractionthe aqueous solution was extracted with EtOAc (3×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ab5c62a81f84df4bae5f88c3c8f318e
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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