{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester → (1-[4-(8-Methoxy-7-nitro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037360Notes

Reaction equation

HRID 1037360 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15](C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].I[C:38]1[C:47](=[O:48])[C:46]2[C:41](=[C:42]([O:52][CH3:53])[C:43]([N+:49]([O-:51])=[O:50])=[CH:44][CH:45]=2)[O:40][C:39]=1[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:38]3[C:47](=[O:48])[C:46]4[C:41](=[C:42]([O:52][CH3:53])[C:43]([N+:49]([O-:51])=[O:50])=[CH:44][CH:45]=4)[O:40][C:39]=3[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 67067635{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 670678843-Iodo-8-methoxy-7-nitro-2-phenyl-chromen-4-one

Product 1

HCID 67067940(1-[4-(8-Methoxy-7-nitro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl esterYield 72%

Procedure

Following the procedure used to prepare {1-[4-(6-fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester, 3-iodo-8-methoxy-7-nitro-2-phenyl-chromen-4-one was reacted to give the title compound as a yellow solid (390 mg, 72%). LCMS (Method G): RT=4.47 min, [M+H]+=543.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-45199dbfb7ad4b2292a3b47cc0e2b7d4
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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