4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → (1-{4-[7-Methoxy-4-oxo-2-phenyl-8-(1H-pyrazol-4-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037345Notes

Reaction equation

HRID 1037345 reaction equation
C(OC(=O)NC1(C2C=CC(C3C(=O)C4C(=CC([C:29]5[NH:30][N:31]=[CH:32][CH:33]=5)=CC=4)OC=3C3C=CC=CC=3)=CC=2)CCC1)(C)(C)C.[C:41]([O:45][C:46](=[O:78])[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)[C:63]([O:69][CH3:70])=[CH:64][CH:65]=4)[O:60][C:59]=3[C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)=[CH:54][CH:53]=2)[CH2:51][CH2:50][CH2:49]1)([CH3:44])([CH3:43])[CH3:42].CC1(C)C(C)(C)OB(C2C=NNC=2)O1>>[C:41]([O:45][C:46](=[O:78])[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:33]5[CH:29]=[N:30][NH:31][CH:32]=5)[C:63]([O:69][CH3:70])=[CH:64][CH:65]=4)[O:60][C:59]=3[C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)=[CH:54][CH:53]=2)[CH2:51][CH2:50][CH2:49]1)([CH3:44])([CH3:43])[CH3:42]

Participants

4

Reactant 3

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67067641(1-{4-[4-oxo-2-phenyl-7-(2H-pyrazol-3-yl)-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 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 67067864(1-{4-[7-Methoxy-4-oxo-2-phenyl-8-(1H-pyrazol-4-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl esterYield 52%

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-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (100 mg, 0.173 mmol) was reacted with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole to give the title compound (51 mg, 52%). LCMS (Method H): RT=3.77 min, [M+H]+=564.

Sources & evidence

ORD record
ord-1e854d1eb87445f2b34b0ff0d055b6c9
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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