Water → HCID 71293803, compound

HRID 2036027Notes

Reaction equation

HRID 2036027 reaction equation
O.[CH:2]1[N:6]=[CH:5][N:4]2[C@H:7]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][C:11]=3[F:18])[CH2:8][CH2:9][C:3]=12.C([O:23]O)(C)(C)C>[Fe](Cl)(Cl)Cl.N1C=CC=CC=1>[F:18][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:10]=1[C@H:7]1[N:4]2[CH:5]=[N:6][CH:2]=[C:3]2[C:9](=[O:23])[CH2:8]1)[C:14]#[N:15]

Participants

6

Reactant 3

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 66885310HCID 66885310, compound

Product 1

HCID 71293803HCID 71293803, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 1049PyridineSolvent

Procedure

To a 500 mL round-bottomed flask equipped with a water condensor is added (S)-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-fluorobenzonitrile (6.0 g, 26.3 mmol) and pyridine (32.6 mL). To the solution is added iron(III) chloride (0.21 g, 1.32 mmol and tert-butyl hydroperoxide (10.9 mL, 79 mmol). The reaction is heated to reflux and stirred for 5 hours. The reaction is allowed to cool to room temperature and is then filtered through celite. The collect filtrate is concentrated under reduced pressure. The obtained residue is purified by RP-HPLC (XBridge, C8 H2O (0.1% NH4OH)/CH3CN) to give 1.5 g of the entitled product. MS (m+1)=242.1; LCMS condition B, retention time=0.97 min; 1H NMR (400 MHz, CDCl3) δ ppm 3.12 (dd, 1H), 3.80 (dd, 1H), 6.04 (dd, 1H), 7.14 (t, 1H), 7.48-7.57 (m, 2H), 7.61 s, 1H, 7.72 s, 1H.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux
  3. filtrationis then filtered through celite
  4. concentrationThe collect filtrate is concentrated under reduced pressure
  5. customThe obtained residue is purified by RP-HPLC (XBridge, C8 H2O (0.1% NH4OH)/CH3CN)

Sources & evidence

ORD record
ord-89f8932d224647d784dd04b6b6c805a9
Source dataset
uspto-grants-2013_11
Patent number
US08575160B2

Reaction notes

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