Sodium hydride → HCID 86650540, compound

HRID 2066636Notes

Reaction equation

HRID 2066636 reaction equation
[CH3:1][C:2]1([CH2:13][OH:14])[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1.[H-].[Na+].[Br:17][C:18]1[CH:23]=[N:22][C:21](Br)=[CH:20][N:19]=1>CN(C=O)C>[Br:17][C:18]1[N:19]=[CH:20][C:21]([O:14][CH2:13][C:2]2([CH3:1])[O:6][C:5]3=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]3[CH2:3]2)=[N:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 114704212,5-dibromopyrazineHCID 23081240(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methanol

Product 1

HCID 86650540HCID 86650540, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of alcohol 101 (see Example 2M) (350 mg, 1.76 mmol) in anhydrous DMF (7 mL) under N2 at 0° C. was treated with 60% NaH (104 mg, 2.60 mmol) and 2,5-dibromopyrazine (837 mg, 3.52 mmol), then quickly degassed and resealed under N2. After stirring at room temperature for 3 h, the reaction was cooled (CO2/acetone), quenched with ice/aqueous NaHCO3 (20 mL), added to brine (80 mL), and extracted with CH2Cl2 (6×100 mL). The combined extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with CH2Cl2 firstly gave foreruns, and then further elution with 0-2% EtOAc/CH2Cl2 gave 2-{[(5-bromo-2-pyrazinyl)oxy]methyl}-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole (104) (428 mg, 68%) as a white solid: mp (MeOH/CH2Cl2/hexane) 198-200° C.; 1H NMR [(CD3)2SO] δ 8.44 (d, J=1.3 Hz, 1H), 8.16 (d, J=1.3 Hz, 1H), 8.14 (s, 1H), 4.62 (s, 2H), 4.40 (d, J=11.0 Hz, 1H), 4.19 (d, J=11.0 Hz, 1H), 1.70 (s, 3H). Anal. (C11H10BrN5O4) C, H, N.

Workup

  1. customat 0° C.
  2. customquickly degassed
  3. temperaturethe reaction was cooled (CO2/acetone)
  4. customquenched with ice/aqueous NaHCO3 (20 mL)
  5. additionadded to brine (80 mL)
  6. extractionextracted with CH2Cl2 (6×100 mL)
  7. customThe combined extracts were evaporated to dryness
  8. customthe residue was chromatographed on silica gel
  9. washElution with CH2Cl2 firstly gave foreruns
  10. washfurther elution with 0-2% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-c34937e21a0e4c73b5c1bc1318620a5b
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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