7H-Pyrrolo[1,2-a]imidazol-7-one,5,6-dihydro-(9CI) → HCID 86669575, compound

HRID 1398519Notes

Reaction equation

HRID 1398519 reaction equation
[C:1]([Mg]Br)#[CH:2].[N:5]1[CH:9]=[CH:8][N:7]2[CH2:10][CH2:11][C:12](=[O:13])[C:6]=12>C1COCC1>[C:1]([C:12]1([OH:13])[C:6]2=[N:5][CH:9]=[CH:8][N:7]2[CH2:10][CH2:11]1)#[CH:2]

Participants

4

Reactant 2

HCID 138098147H-Pyrrolo[1,2-a]imidazol-7-one,5,6-dihydro-(9CI)HCID 178418486HCID 178418486, compound

Product 1

HCID 86669575HCID 86669575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethynylmagnesium bromide (0.5M in THF, 14.6 mL, 7.3 mmol) at 0° C. was added 5H,6H-pyrrolo[1,2-a]imidazol-7-one (900 mg, 4.86 mmol) in THF (10 mL) slowly. The reaction mixture was allowed to warm to RT and stirred for 1 hr. The reaction mixture was quenched with saturated aqueous NH4Cl solution (10 mL) and the organics were removed in vacuo. The product was extracted into EtOAc (10 mL×2) and the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (Biotage), eluting with 3-10% methanol in DCM afforded the title product; 1H NMR (500 MHz, CDCl3) delta 2.55 (1H, s), 2.96 (1H, ddd, J=13.24, 7.57, 4.26 Hz), 3.03-3.12 (1H, m), 3.16-3.22 (1H, m), 4.01 (1H, ddd, J=10.56, 8.12, 4.33 Hz), 4.15 (1H, ddd, J=10.52, 7.29, 6.62 Hz), 6.84 (1H, d, J=1.10 Hz), 7.11 (1H, d, J=0.79 Hz); LC-MS: m/z=+136.9 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl solution (10 mL)
  2. customthe organics were removed in vacuo
  3. extractionThe product was extracted into EtOAc (10 mL×2)
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (Biotage)
  8. washeluting with 3-10% methanol in DCM

Sources & evidence

ORD record
ord-2221bc63e1234f2a83954861ae018474
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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