Diethyl Ether → HCID 67216579, compound

HRID 2036036Notes

Reaction equation

HRID 2036036 reaction equation
[CH3:1][C:2]1([CH3:20])[C@H:9]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][C:11]=2[F:18])[N:5]2[CH:6]=[N:7][CH:8]=[C:4]2[C:3]1=[O:19].[F:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1.CCOCC>C1COCC1>[F:18][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:10]=1[C@@H:9]1[N:5]2[CH:6]=[N:7][CH:8]=[C:4]2[C@:3]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)([OH:19])[C:2]1([CH3:20])[CH3:1])[C:14]#[N:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 67216728HCID 67216728, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 67216579HCID 67216579, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-((R)-6,6-dimethyl-7-oxo-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-fluoro-benzonitrile (157 mg, 0.45 mmol) in THF cooled to −78° C. was added a 2 M solution of 4-fluoro-phenyl-magnesium bromide in ether (0.39 mL, 0.78 mmol). The crude was allowed to warm to room temperature overnight. The crude was quenched with H2O and diluted in EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated. The crude was purified via flash chromatography first with EtOAc/heptane system followed by MeOH/CH2Cl2 to give 160 mg of the entitled product. MS 366.2 (M+H); LCMS condition B, retention time 1.14 min. 1H NMR (400 MHz, CDCl3) δ ppm 0.88 (s, 3H), 1.00 (s, 3H), 5.45 (s, 1H), 6.92 (t, 1H), 7.04 (s, 1H), 7.05-7.13 (m, 2H), 7.32-7.44 (m, 2H), 7.49 (s, 1H), 7.50-7.58 (m, 2H).

Workup

  1. customThe crude was quenched with H2O
  2. additiondiluted in EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified via flash chromatography first with EtOAc/heptane system

Sources & evidence

ORD record
ord-c4bdfe3dfa7a4e9a9c0547d33db6c5a5
Source dataset
uspto-grants-2013_11
Patent number
US08575160B2

Reaction notes

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