Potassium Carbonate → 4-(5-Bromo-2-ethynylimidazo[1,2-a]pyrazin-8-yl)morpholine

HRID 1772718Notes

Reaction equation

HRID 1772718 reaction equation
[Br:1][C:2]1[N:7]2[CH:8]=[C:9]([CH:11]=O)[N:10]=[C:6]2[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:4][CH:3]=1.[C:19]([O-])([O-])=O.[K+].[K+].COP(C(=[N+]=[N-])C(=O)C)(=O)OC>CO>[Br:1][C:2]1[N:7]2[CH:8]=[C:9]([C:11]#[CH:19])[N:10]=[C:6]2[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1177281135-Bromo-8-morpholinoimidazo[1,2-a]pyrazine-2-carbaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 1177279194-(5-Bromo-2-ethynylimidazo[1,2-a]pyrazin-8-yl)morpholine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred suspension of compound 2a (562 mg, 1.80 mmol) in MeOH (10 mL), solid K2CO3 (0.749 g, 5.41 mmol) was added followed by dimethyl(1-diazo-2-oxopropyl)phosphonate (382 mg, 1.98 mmol) in MeOH (5 mL). The reaction was stirred at rt for 12 h and concentrated. The residue was dissolved in DCM (40 mL) and washed with water (25 mL). The aqueous layer was extracted with DCM (3×20 mL). The combined organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was triturated with 1:1 EtOAc/heptane, filtered and dried to give compound 80a as an off-white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C12H11BrN4O: 307.0 (M+H). found: 307.1.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DCM (40 mL)
  4. washwashed with water (25 mL)
  5. extractionThe aqueous layer was extracted with DCM (3×20 mL)
  6. washThe combined organic extracts were washed with brine (25 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was triturated with 1:1 EtOAc/heptane
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-bf6991e9ec0b45e1b37fd7f12b5de05a
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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