3-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride) → HCID 136027632, compound

HRID 1428908Notes

Reaction equation

HRID 1428908 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]([F:44])([F:43])[O:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1>>[O:29]=[C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:36]3[CH:37]=[CH:38][CH:39]=[C:34]([O:33][C:32]([F:31])([F:43])[F:44])[CH:35]=3)[CH:17]=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]1

Participants

3

Reactant 2

HCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 68487682HCID 68487682, compound

Product 1

HCID 136027632HCID 136027632, 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 3-trifluoromethoxyphenylboronic acid in step C. MS (ESI): mass calcd. for C19H11F3N4O4, 416.1; m/z found, 417.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.06-12.92 (m, 2H), 8.99 (s, 1H), 8.39 (s, 1H), 8.28 (s, 1H), 8.22 (dd, J=8.4, 1.8 Hz, 1H), 7.86 (d, J=8.0 Hz, 1H), 7.79 (s, 2H), 7.66 (t, J=8.0 Hz, 1H), 7.46-7.40 (m, 1H).

Sources & evidence

ORD record
ord-be8d6c13d66a4c6cb22a67594fff599a
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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