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

HRID 1037177Notes

Reaction equation

HRID 1037177 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].[Br:37][C:38]1[C:39]([O:56][CH3:57])=[CH:40][CH:41]=[C:42]2[C:47]=1[O:46][C:45]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[C:44](I)[C:43]2=[O:55]>>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:44]3[C:43](=[O:55])[C:42]4[C:47](=[C:38]([Br:37])[C:39]([O:56][CH3:57])=[CH:40][CH:41]=4)[O:46][C:45]=3[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=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 670676878-Bromo-3-iodo-7-methoxy-2-phenyl-chromen-4-one

Product 1

HCID 67067708{1-[4-(8-Bromo-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 40%

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, 8-bromo-3-iodo-7-methoxy-2-phenyl-chromen-4-one (198 mg, 0.434 mmol) was reacted to give the title compound (100 mg, 40%). 1H NMR (400 MHz, CDCl3): δ 8.27-8.22 (d, 1H), 7.53-7.19 (m, 9H), 7.08-7.03 (d, 1H), 5.06 (s, 1H), 4.06 (s, 3H), 2.58-1.76 (m, 6H), 1.46-1.18 (m, 9H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-e3155d69f16149439a05ea94d6bbdee6
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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