3-Pyridinylboronic acid → {1-[4-(4-oxo-2-phenyl-8-pyridin-3-yl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037285

Reaction equation

HRID 1037285 reaction equation
C(OC(=O)NC1(C2C=CC(C3C(=O)[C:26]4[C:21](=[CH:22][C:23]([C:29]5[NH:30]N=CC=5)=CC=4)OC=3C3C=CC=CC=3)=CC=2)CCC1)(C)(C)C.[C:41]([O:45][C:46](=[O:76])[NH:47][C:48]1([C:52]2[CH:57]=[CH:56][C:55]([C:58]3[C:67](=[O:68])[C:66]4[C:61](=[C:62](Br)[CH:63]=[CH:64][CH:65]=4)[O:60][C:59]=3[C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)=[CH:54][CH:53]=2)[CH2:51][CH2:50][CH2:49]1)([CH3:44])([CH3:43])[CH3:42].N1C=CC=C(B(O)O)C=1>CCOC(C)=O>[C:41]([O:45][C:46](=[O:76])[NH:47][C:48]1([C:52]2[CH:57]=[CH:56][C:55]([C:58]3[C:67](=[O:68])[C:66]4[C:61](=[C:62]([C:23]5[CH:29]=[N:30][CH:26]=[CH:21][CH:22]=5)[CH:63]=[CH:64][CH:65]=4)[O:60][C:59]=3[C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)=[CH:54][CH:53]=2)[CH2:51][CH2:50][CH2:49]1)([CH3:44])([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 27343783-Pyridinylboronic acidHCID 67067641(1-{4-[4-oxo-2-phenyl-7-(2H-pyrazol-3-yl)-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 67067700{1-[4-(8-Bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 67067949{1-[4-(4-oxo-2-phenyl-8-pyridin-3-yl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure used to prepare (1-{4-[4-oxo-2-phenyl-7-(2H-pyrazol-3-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester, {1-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted with pyridine-3-boronic acid to give a crude residue which was insoluble in the EtOAc/aqueous work-up mixture. The solid was collected by filtration and air dried to give the title compound as a tan solid (44 mg, 59%). LCMS (Method B): RT=4.74 min, [M+H]+=545.

Workup

  1. customto give a crude residue which
  2. filtrationThe solid was collected by filtration and air
  3. customdried

Sources & evidence

ORD record
ord-d89eff26b7da4ade9fa78934f01162ca
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Linked notes

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