Methanesulfonamide → 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-N-(methylsulfonyl)-1H-indole-3-carboxamide

HRID 338521Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([OH:23])[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.C(C(OC1C(OC(C(C)(C)C)=O)=C(I)C=CC=1)=O)(C)(C)C.[CH3:45][S:46]([NH2:49])(=[O:48])=[O:47]>C(OC(C)C)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([NH:49][S:46]([CH3:45])(=[O:48])=[O:47])=[O:12])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([C:19]2([OH:23])[CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carbaldehyde (40 mg, 0.123 mmol), Bis(tert-butylcarbonyloxy)iodobenzene (104 mg, 0.256 mmol) in isopropyl acetate (2 mL) was added methanesulfonamide (12 mg, 0.126 mmol). After stirring 5 minutes, Bis[rhodium(α,α,α′,α′-tetramethyl-1,3-benzenedipropionic acid)] (5 mg, 0.007 mmol) was added and heated to 80° C. overnight. The mixture was concentrated to give a crude residue, which was purified by preparative HPLC to afford the title compound (6.6 mg, 13%) as a yellow solid.

Workup

concentrationThe mixture was concentrated
customto give a crude residue, which
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-fd553db09de74a4e80ee05974710c584
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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