{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester → 2-Methyl-propane-2-sulfinic acid {3-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-oxetan-3-yl}-amide

HRID 1037324Notes

Reaction equation

HRID 1037324 reaction equation
C(OC(=O)NC1(C2C=CC(C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=CC=2)CCC1)(C)(C)C.[Br:37][C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:47]=1[O:46][C:45]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[C:44](I)[C:43]2=[O:55].CC1(C)C(C)(C)OB([C:64]2[CH:69]=[CH:68][C:67]([C:70]3([NH:74][S:75]([C:77]([CH3:80])([CH3:79])[CH3:78])=[O:76])[CH2:73][O:72][CH2:71]3)=[CH:66][CH:65]=2)O1>>[Br:37][C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:47]=1[O:46][C:45]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[C:44]([C:64]1[CH:65]=[CH:66][C:67]([C:70]3([NH:74][S:75]([C:77]([CH3:80])([CH3:79])[CH3:78])=[O:76])[CH2:73][O:72][CH2:71]3)=[CH:68][CH:69]=1)[C:43]2=[O:55]

Participants

4

Reactant 3

HCID 67067635{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 670677418-Bromo-3-iodo-2-phenyl-chromen-4-oneHCID 670678002-Methyl-propane-2-sulfinic acid {3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenyl]-oxetan-3-yl}-amide

Product 1

HCID 670677152-Methyl-propane-2-sulfinic acid {3-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-oxetan-3-yl}-amideYield 55%

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, 8-bromo-3-iodo-2-phenyl-chromen-4-one and 2-methyl-propane-2-sulfinic acid {3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenyl]-oxetan-3-yl}-amide were reacted to give the title compound as a tan solid (59 mg, 55%). LCMS (Method B): RT=5.02 min, [M+H]+=552/554.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-4bba5419480c42998dde40eab245ae18
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…