p-Toluenesulfonic acid → 6-Bromo-1-(oxan-4-yl)-1H-benzimidazole

HRID 1399831Notes

Reaction equation

HRID 1399831 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([NH2:15])=[CH:4][CH:3]=1.[CH3:16]C1C=CC(S(O)(=O)=O)=CC=1>C(OC)(OC)OC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:15]=[CH:16][N:8]([CH:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 65343320HCID 65343320, compound

Product 1

HCID 529880396-Bromo-1-(oxan-4-yl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of compound 5-bromo-N1-(tetrahydro-2H-pyran-4-yl)benzene-1,2-diamine (500 mg, 1.852 mmol) in HC(OMe)3 (2 mL) was added TsOH (15 mg, 0.0789 mmol). The reaction mixture was stirred at 100° C. for 12 h. The reaction mixture was extracted with DCM washed with water and the organic layer dried over sodium sulfate which was removed by filtration. After concentration of the filtrate, the crude product was purified by column (201 mg, 38.53%). LCMS (m/z): 281.0, 283.0 (M+1).

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. washwashed with water
  3. dry with materialthe organic layer dried over sodium sulfate which
  4. customwas removed by filtration
  5. customAfter concentration of the filtrate, the crude product was purified by column (201 mg, 38.53%)

Sources & evidence

ORD record
ord-18fdacb985034e23b823682fc5ba3386
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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