4-(Pyridin-4-yl)aniline → 2-(4-Pyridin-4-yl-phenylsulfamoyl)-indole-1-carboxylic acid tert-butyl ester

HRID 1693127Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (4-pyridine-4-yl)aniline (CAS: 13296-04-3, 0.054 g) and 2-chlorosulfonyl-indole-1-carboxylic acid tert-butyl ester (0.120 g; cf. Shankar, Bandarpalle B.; Gilbert, Eric; Rizvi, Razia K.; Huang, Chunli; Kozlowski, Joseph A.; McCombie, Stuart; Shih, Neng-Yang. WO 2006002133) in 1,2-dichlorethane (5.0 ml) was added DMAP (0.047 g). The reaction mixture was stirred at 50° C. for 3 h and chromatographed on silica gel using dichloromethanelethyl acetate as eluent to obtain the desired compound (0.070 g) as a colorless powder. MS (ISP): 450.4 (M+H)+

Workup

customchromatographed on silica gel using dichloromethanelethyl acetate as eluent

Sources & evidence

ORD record: ord-6c6d3ac094cb49f498f44139d485c99d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158655B2

Reaction notes

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