3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(1-Amino-cyclobutyl)-phenyl]-8-bromo-7-methoxy-2-phenyl-chromen-4-one

HRID 1037178Notes

Reaction equation

HRID 1037178 reaction equation
NC1(C2C=CC(C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=CC=2)CCC1.C(OC(=O)[NH:36][C:37]1([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[C:51]([Br:60])[C:52]([O:58][CH3:59])=[CH:53][CH:54]=4)[O:49][C:48]=3[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C>>[NH2:36][C:37]1([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[C:51]([Br:60])[C:52]([O:58][CH3:59])=[CH:53][CH:54]=4)[O:49][C:48]=3[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[CH:45][CH:46]=2)[CH2:38][CH2:39][CH2:40]1

Participants

3

Reactant 2

HCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067708{1-[4-(8-Bromo-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510306923-[4-(1-Amino-cyclobutyl)-phenyl]-8-bromo-7-methoxy-2-phenyl-chromen-4-oneYield 78%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(8-bromo-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (20 mg, 0.035 mmol) was reacted to give the title compound (13 mg, 78%). LCMS (Method E): RT=3.93 min, [M+H]+=476/478. 1H NMR (400 MHz, DMSO-d6): δ 8.05 (d, J=8.7 Hz, 1H), 7.42-7.26 (m, 8H), 7.09 (d, J=7.8 Hz, 2H), 3.99 (s, 3H), 2.56 (bs, 2H), 2.37-2.25 (m, 2H), 2.10-1.87 (m, 3H), 1.66-1.53 (m, 1H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-d15925bfe9fa4fd0af015ab508bfd87d
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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