1H-Indol-6-ylboronic acid → HCID 136027570, compound

HRID 1428840Notes

Reaction equation

HRID 1428840 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.[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37](B(O)O)[CH:38]=2)[CH:33]=[CH:32]1>>[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:16]3[CH:17]=[C:18]4[C:13](=[CH:14][CH:15]=3)[N:12]=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]3)[NH:20][C:19]4=[O:29])[CH:38]=2)[CH:33]=[CH:32]1

Participants

3

Reactant 2

HCID 27632051H-Indol-6-ylboronic acidHCID 68487682HCID 68487682, compound

Product 1

HCID 136027570HCID 136027570, 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 indole-6-boronic acid in step C. MS (ESI): mass calcd. for C20H13N5O3, 371.1; m/z found, 372.1 [M+H]+. 1H NMR (600 MHz, DMSO-d6): 13.01 (s, 1H), 12.86 (s, 1H), 11.23 (s, 1H), 8.99 (s, 1H), 8.37 (s, 1H), 8.27 (s, 1H), 8.20 (s, 1H), 7.77 (s, 2H), 7.67 (d, J=8.2 Hz, 1H), 7.43 (s, 2H), 6.48 (s, 1H).

Sources & evidence

ORD record
ord-c15608f662294d2399e1614bcb4182af
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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