2-(Methylsulfonyl)phenylboronic Acid → tert-butyl (1-(4-(8-(2-(methylsulfonyl)phenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate

HRID 1037419Notes

Reaction equation

HRID 1037419 reaction equation
NC1(C2C=CC(C3C(=O)C4C(OC=3C3C=CC=CC=3)=C(C3C=NN(CC(C)C)C=3)N=CC=4)=CC=2)CCC1.Cl[C:39]1[N:40]=[CH:41][CH:42]=[C:43]2[C:48](=[O:49])[C:47]([C:50]3[CH:55]=[CH:54][C:53]([C:56]4([NH:60][C:61](=[O:67])[O:62][C:63]([CH3:66])([CH3:65])[CH3:64])[CH2:59][CH2:58][CH2:57]4)=[CH:52][CH:51]=3)=[C:46]([C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=3)[O:45][C:44]=12.[CH3:74][S:75]([C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][C:79]=1B(O)O)(=[O:77])=[O:76]>>[CH3:74][S:75]([C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][C:79]=1[C:39]1[N:40]=[CH:41][CH:42]=[C:43]2[C:48](=[O:49])[C:47]([C:50]3[CH:51]=[CH:52][C:53]([C:56]4([NH:60][C:61](=[O:67])[O:62][C:63]([CH3:66])([CH3:64])[CH3:65])[CH2:57][CH2:58][CH2:59]4)=[CH:54][CH:55]=3)=[C:46]([C:68]3[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=3)[O:45][C:44]=12)(=[O:77])=[O:76]

Participants

4

Reactant 3

HCID 27735392-(Methylsulfonyl)phenylboronic AcidHCID 670677673-(4-(1-aminocyclobutyl)phenyl)-8-(1-isobutyl-1H-pyrazol-4-yl)-2-phenyl-4H-pyrano[2,3-c]pyridin-4-oneHCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

Product 1

HCID 67067938tert-butyl (1-(4-(8-(2-(methylsulfonyl)phenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamateYield 62%

Procedure

Following the procedure used to prepare 3-(4-(1-aminocyclobutyl)phenyl)-8-(1-isobutyl-1H-pyrazol-4-yl)-2-phenyl-4H-pyrano[2,3-c]pyridin-4-one, tert-butyl (1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl)carbamate was reacted with (2-(methylsulfonyl)phenyl)boronic acid to give the title compound (40 mg, 62%). LCMS (Method I): RT=7.31 min, [M+2]+=567 (-tBu).

Sources & evidence

ORD record
ord-608ed4134a6a422f9f0ff3f2025ed324
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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