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

HRID 1037169Notes

Reaction equation

HRID 1037169 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](=[CH:42][C:43]([CH3:51])=[C:44]([O:49][CH3:50])[CH:45]=2)[O:40][C:39]=1[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=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](=[CH:42][C:43]([CH3:51])=[C:44]([O:49][CH3:50])[CH:45]=4)[O:40][C:39]=3[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=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 670677863-Iodo-6-methoxy-7-methyl-2-phenyl-chromen-4-one

Product 1

HCID 68227223{1-[4-(6-Methoxy-7-methyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 41%

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-6-methoxy-7-methyl-2-phenyl-chromen-4-one (78 mg, 0.20 mmol) was reacted to give the title compound (40 mg, 41%). 1H NMR (400 MHz, CDCl3): δ 7.56 (s, 1H), 7.41-7.17 (m, 10H), 5.04 (s, 1H), 3.94 (s, 3H), 2.60-2.46 (m, 4H), 2.39-2.35 (m, 3H), 2.13-2.00 (m, 1H), 1.90-1.76 (m, 1H), 1.48-1.10 (m, 9H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-f019b3a43331492dbba33fc5b248f2c6
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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