4-Nitrobenzoyl isothiocyanate → N-((3-bromo-5-(2-hydroxyethyl)-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)carbamothioyl)-4-nitrobenzamide

HRID 455620Notes

Reaction equation

[NH2:1][C:2]1([CH2:18][CH2:19][OH:20])[C:15]2[C:10](=[N:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[O:9][C:8]2[C:3]1=[CH:4][C:5]([I:17])=[CH:6][CH:7]=2.[N+:21]([C:24]1[CH:34]=[CH:33][C:27]([C:28]([N:30]=[C:31]=[S:32])=[O:29])=[CH:26][CH:25]=1)([O-:23])=[O:22]>C1COCC1>[Br:16][C:13]1[CH:14]=[C:15]2[C:2]([NH:1][C:31]([NH:30][C:28](=[O:29])[C:27]3[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:34][CH:33]=3)=[S:32])([CH2:18][CH2:19][OH:20])[C:3]3[C:8](=[CH:7][CH:6]=[C:5]([I:17])[CH:4]=3)[O:9][C:10]2=[N:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-(5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)ethanol (0.930 g, 2.080 mmol) in THF (20.80 ml) was added cooled to 0° C. and solid 4-nitrobenzoyl isothiocyanate (0.442 g, 2.122 mmol) was added. The reaction mixture was stirred at 0° C. for 20 min. The reaction mixture was concentrated under reduced pressure to yield N-((3-bromo-5-(2-hydroxyethyl)-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)carbamothioyl)-4-nitrobenzamide as a yellow solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-db604cd39a73472eb0269832955d8a09
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Reaction notes

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