Pyridine → HCID 59426182, compound

HRID 907184Notes

Reaction equation

HRID 907184 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[C:5]([C:16]#[N:17])=[C:4]1[N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:2].N1C=CC=CC=1.[CH:30]1([S:33](Cl)(=[O:35])=[O:34])[CH2:32][CH2:31]1>ClCCl>[CH:30]1([S:33]([N:21]2[CH2:20][CH2:19][N:18]([C:4]3[N:3]([CH2:1][CH3:2])[C:11]4[C:6]([C:5]=3[C:16]#[N:17])=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:15])[F:13])[CH:10]=4)[CH2:23][CH2:22]2)(=[O:35])=[O:34])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2760919Cyclopropanesulfonyl chlorideHCID 59426299HCID 59426299, compound

Product 1

HCID 59426182HCID 59426182, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-ethyl-2-piperazin-1-yl-6-(trifluoromethyl)-1H-indole-3-carbonitrile (32 mg, 0.1 mmol), pyridine (0.1 mL) in dichloromethaene (1.0 mL) was added cyclopropanesulfonyl chloride (28 mg, 0.2 mmol) and the mixture was stirred at room temperature overnight. This was then diluted with dichloromethane (5 mL), washed with HCl (2 N, 2×2 mL), water (2×5 mL) and brine (5 mL) and chromatographed over silica gel (dichloromethane/ethyl acetate, 9/1) to provide 2-[4-(cyclopropylsulfonyl)piperazin-1-yl]-1-ethyl-6-(trifluoromethyl)-1H-indole-3-carbonitrile, compound 842 (30 mg, 70%).

Workup

  1. washwashed with HCl (2 N, 2×2 mL), water (2×5 mL) and brine (5 mL)
  2. customchromatographed over silica gel (dichloromethane/ethyl acetate, 9/1)

Sources & evidence

ORD record
ord-0f59fb88f5874226a7c926dab4c7e492
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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