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

HRID 1037181Notes

Reaction equation

HRID 1037181 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:29]#[N:30])[CH:25]=4)[O:20][C:19]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:38]([O:42]C(=O)NC1(C2C=CC(C3C(=O)C4C(=CC(OC)=C(Br)C=4)OC=3C3C=CC=CC=3)=CC=2)CCC1)(C)(C)C>>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][C:23]([O:42][CH3:38])=[C:24]([C:29]#[N:30])[CH:25]=4)[O:20][C:19]=3[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 67067657{1-[4-(6-cyano-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 67067774{1-[4-(6-bromo-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 67067795{1-[4-(6-Cyano-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 77%

Procedure

Following the procedure used to prepare {1-[4-(6-cyano-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester, {1-[4-(6-bromo-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (115 mg, 0.20 mmol) was reacted to give the title compound (81 mg, 77%). 1H NMR (400 MHz, CDCl3): δ 8.53 (s, 1H), 7.45-7.14 (m, 9H), 7.00 (s, 1H), 5.05 (s, 1H), 4.05 (s, 3H), 2.60-2.39 (m, 4H), 2.16-2.00 (m, 1H), 1.92-1.77 (m, 1H), 1.56-1.14 (m, 9H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-04bd96782cfe4aa6b169fddfeb34ad07
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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