Methanesulfonyl chloride → 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-5-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-pyrrolo-[3,2-c]pyridine

HRID 1790032Notes

Reaction equation

HRID 1790032 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][N:13]([S:26]([CH3:25])(=[O:28])=[O:27])[CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 220385001-(2-chlorophenyl)-2-(4-methoxyphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 220385261-(2-chlorophenyl)-2-(4-methoxyphenyl)-5-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-pyrrolo-[3,2-c]pyridineYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an 8-mL vial charged with piperidinomethyl polystyrene (3.57 mmol/g, 99.2 mg, 0.354 mmol) and a solution of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2), 40.0 mg, 0.118 mmol) in 4 mL dichloromethane was added methanesulfonyl chloride (18.2 μL, 0.236 mmol). The reaction mixture was mixed by orbital shaking for 4 h. The solid was removed by filtration. The filtrate was evaporated, and the residue was purified by preparative reversed-phase HPLC to give a solid (19.8 mg, 40%): Rf=0.20 (1:2 EtOAc/hexanes).

Workup

  1. additionThe reaction mixture was mixed
  2. customThe solid was removed by filtration
  3. customThe filtrate was evaporated
  4. customthe residue was purified by preparative reversed-phase HPLC

Sources & evidence

ORD record
ord-6e6784a81a91463a8f895bb1e9274f2a
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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