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

HRID 1037202Notes

Reaction equation

HRID 1037202 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](=[CH:51][CH:52]=[C:53]([Br:58])[CH:54]=4)[O:49][C:48]=3[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=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](=[CH:51][CH:52]=[C:53]([Br:58])[CH:54]=4)[O:49][C:48]=3[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=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 67067709{1-[4-(6-Bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510308793-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-6-bromo-chromen-4-oneYield 80%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(6-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a pale yellow solid (26 mg, 80%). 1H NMR (400 MHz, DMSO-d6): δ 8.18 (d, J=2 Hz, 1H), 8.02 (dd, J=2 and 9 Hz, 1H), 7.75 (d, J=9 Hz, 1H), 7.45-7.31 (m, 7H), 7.17-7.12 (m, 2H), 2.44-2.34 (m, 2H), 2.17-2.07 (m, 2H), 2.05-1.95 (m, 1H), 1.71-1.61 (m, 1H). LCMS (Method F): RT=9.86 min, [M+H]+=446/448.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-0daf60ce77764665bb3bbf86e02db98c
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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