3-Chlorobenzenesulphonyl chloride → HCID 10412212, compound

HRID 1828232Notes

Reaction equation

[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[CH:16]=[CH:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1>[N+](C1C=CC=CC=1)([O-])=O.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[C:16]([S:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([Cl:23])[CH:25]=2)(=[O:32])=[O:31])=[CH:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-[(1-benzylpyrrolidin-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine (2.0 g, 6.86 mmol), 3-chlorophenylsulfonyl chloride (1.63 g, 7.55 mmol) and silver trifluoromethanesulfonate (AgOTf) (2.32 g, 8.92 mmol) in nitrobenzene is heated at 100° C. under a nitrogen atmosphere for 36 h, cooled to room temperature, quenched with 10% aqueous sodium carbonate, and extracted with CH2Cl2. The extracts are combined, washed sequentially with water and brine and concentrated in vacuo. The resultant residue is purified by flash column chromatography (0–5% methanol in CH2Cl2 as eluent) to afford the title compound as a semi-solid, 865 mg (27% yield), identified by HNMR and mass spectral analyses.

Workup

temperaturecooled to room temperature
customquenched with 10% aqueous sodium carbonate
extractionextracted with CH2Cl2
washwashed sequentially with water and brine
concentrationconcentrated in vacuo
customThe resultant residue is purified by flash column chromatography (0–5% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record: ord-dfaf401ac2984cd99c28986710cd5cc4
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07057039B2

Reaction notes

Loading…