5-fluoro-1-methyl-1H-indole-2-sulfonyl chloride → 4-[4-(5-Fluoro-1-methyl-1H-indole-2-sulfonylamino)-3-methanesulfonyl-phenyl]piperidine-1-carboxylic acid tert-butyl ester

HRID 1693129Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH3:35])[C:30]([S:36](Cl)(=[O:38])=[O:37])=[CH:29]2>ClCCCl.CN(C1C=CN=CC=1)C.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:36]([C:30]3[N:31]([CH3:35])[C:32]4[C:28]([CH:29]=3)=[CH:27][C:26]([F:25])=[CH:34][CH:33]=4)(=[O:38])=[O:37])=[C:16]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(4-amino-3-methanesulfonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (cf. Example 24e, 0.048 g) in 1,2-dichloroethane (3.0 ml) was added 5-fluoro-1-methyl-1H-indole-2-sulfonyl chloride (0.035 g) and DMAP (0.025 g). The reaction mixture was stirred at 80° C. for 72 h, diluted with dichloromethane (2 ml) and chromatographed on silica gel using dichloromethane/ethyl acetate as eluent to obtain the title compound (0.019 g) as an off-white foam. MS (ISN): 564.3 (M−H)−

Workup

customchromatographed on silica gel

Sources & evidence

ORD record: ord-9e2c7dd028b64befaa8558236a21f277
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158655B2

Reaction notes

Loading…