Methanesulfonyl chloride → 4-(4-Bromo-pyrazol-1-yl)-1-methanesulfonyl-piperidine

HRID 2400332Notes

Reaction equation

HRID 2400332 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[N:5][N:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.CCN(C(C)C)C(C)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>CC#N>[Br:2][C:3]1[CH:4]=[N:5][N:6]([CH:8]2[CH2:13][CH2:12][N:11]([S:24]([CH3:23])(=[O:26])=[O:25])[CH2:10][CH2:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 534078484-(4-bromo-1H-pyrazol-1-yl)piperidine hydrochloride

Product 1

HCID 681624404-(4-Bromo-pyrazol-1-yl)-1-methanesulfonyl-piperidineYield 86.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(4-bromopyrazol-1-yl)piperidine hydrochloride (380 mg, 1.43 mmol) in CH3CN (10 ml) at 0° C. was added DIPEA (0.75 mlml, 4.3 mmol) followed by methanesulphonyl chloride (0.11 ml, 1.43 mmol), stirred at 0° C. for 1 hour then allowed to warm up to RT over 1 hour. The reaction then partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give the product (380 mg), which was used without further purification 1H NMR (400 MHz, Me-d3-OD): 7.84 (1H, s), 7.50 (1H, s), 4.40-4.27 (1H, m), 3.86 (2H, d), 3.05-2.93 (2H, m), 2.90 (3H, s), 2.25-2.01 (4H, m).

Workup

  1. temperatureto warm up to RT over 1 hour
  2. customThe reaction
  3. customthen partitioned between water and EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d57133959bca40149620ff56cd488dd2
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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