4-Fluorophenylboronic acid → HCID 136027600, compound

HRID 1428900Notes

Reaction equation

HRID 1428900 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:20](COCC[Si](C)(C)C)[C:19](=[O:29])[C:18]3[C:13](=[CH:14][CH:15]=[C:16](I)[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[F:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1>>[F:31][C:32]1[CH:37]=[CH:36][C:35]([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([N:9]2[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]2)[NH:20][C:19]3=[O:29])=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 68487682HCID 68487682, compound

Product 1

HCID 136027600HCID 136027600, compound

Procedure

The titled compound was prepared in a manner analogous to Example 69, steps C-E, using 1-[6-iodo-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (Example 69 product from step B) and 4-fluorophenylboronic acid in step C. MS (ESI): mass calcd. for C18H11FN4O3, 350.1; m/z found, 351.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.01 (br s, 1H), 12.92 (br s, 1H), 8.98 (s, 1H), 8.32 (s, 1H), 8.28 (s, 1H), 8.16 (dd, J=8.5, 2.2 Hz, 1H), 7.88-7.82 (m, 2H), 7.79 (s, 1H), 7.37-7.32 (m, 2H).

Sources & evidence

ORD record
ord-29dfc37dc4424564a2ab9e16c51051c5
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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