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

HRID 1037163Notes

Reaction equation

HRID 1037163 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:51][CH3:52])[C:43]([O:49][CH3:50])=[CH:44][CH:45]=2)[O:40][C:39]=1[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=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:51][CH3:52])[C:43]([O:49][CH3:50])=[CH:44][CH:45]=4)[O:40][C:39]=3[C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=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 670676713-Iodo-7,8-dimethoxy-2-phenyl-chromen-4-one

Product 1

HCID 67067980(1-[4-(7,8-dimethoxy-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-7,8-dimethoxy-2-phenyl-chromen-4-one (82 mg, 0.20 mmol) was reacted to give the title compound (41 mg, 41%). 1H NMR (400 MHz, CDCl3): δ 7.56-7.52 (d, 1H), 6.99-6.68 (m, 9H), 6.61-6.56 (d, 1H), 4.61-4.54 (m, 1H), 3.57-3.53 (m, 6H), 2.12-2.00 (m, 4H), 1.65-1.28 (m, 2H), 1.00-0.72 (m, 9H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-60bc5082a20545ce89f639359c77c6ee
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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