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

HRID 1037172Notes

Reaction equation

HRID 1037172 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]([O:50][CH3:51])=[C:44]([CH3:49])[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]([O:50][CH3:51])=[C:44]([CH3:49])[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 670676943-Iodo-7-methoxy-6-methyl-2-phenyl-chromen-4-one

Product 1

HCID 68227545{1-[4-(7-Methoxy-6-methyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 47%

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-7-methoxy-6-methyl-2-phenyl-chromen-4-one (78 mg, 0.20 mmol) was reacted to give the title compound (46 mg, 47%). 1H NMR (400 MHz, CDCl3): δ 8.20-7.98 (m, 1H), 7.44-7.15 (m, 9H), 6.86 (s, 1H), 5.05 (s, 1H), 3.94 (s, 3H), 2.61-2.44 (m, 4H), 2.33-2.28 (m, 3H), 2.14-1.98 (m, 1H), 1.91-1.75 (m, 1H), 1.49-1.12 (m, 9H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-243c84376a0543f18af7df6a6fc441a8
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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