Methanesulfonic Acid → HCID 66608689, compound

HRID 1890909Notes

Reaction equation

HRID 1890909 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:10]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.CS(O)(=O)=O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[N:9]=[CH:8][N:7]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:12]3)[C:6]=2[CH:10]=1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 15163956-Bromo-4-methyl-1H-benzoimidazole

Product 1

HCID 66608689HCID 66608689, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
75 °C

Procedure

6-Bromo-4-methyl-1H-benzo[d]imidazole (1.02 g, 4.83 mmol) was dissolved in tetrahydrofuran (10 mL) at room temperature with stirring under nitrogen. 3,4-Dihydro-2H-pyran (3.5 mL, 38.4 mmol) and methanesulfonic acid (0.032 mL, 0.48 mmol) were added and the resulting mixture heated at 75° C. for 49 h. The resulting mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (50-100% ethyl acetate in hexanes) gave the desired product (1.32 g, 4.47 mmol, 93% yield) as a light yellow solid. MS (ESI) m/z 295.1 [M]+, 297.3 [M+2]+.

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73cb3754d1b44d629501198a2598c59d
Source dataset
uspto-grants-2013_08
Patent number
US08507492B2

Reaction notes

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