Quinoline-3-boronic acid → 1'-methyl-4'-(1H-pyrazol-3-yl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one
Reaction equation
[NH:1]1[CH:5]=[CH:4][C:3](B(O)O)=[N:2]1.N1C2C(=CC=CC=2)C=C(B(O)O)C=1.BrC1C=CC=C2C=1C1(C3=CC4OCOC=4C=C3OC1)C(=O)N2C.Br[C:46]1[CH:54]=[CH:53][CH:52]=[C:51]2[C:47]=1[C:48]1([C:80]3[C:71](=[CH:72][C:73]4[O:78][CH2:77][CH2:76][O:75][C:74]=4[CH:79]=3)[O:70][CH2:69]1)[C:49](=[O:68])[N:50]2[CH:55](C1C=CC=CC=1)C1C=CC=CC=1>>[CH3:55][N:50]1[C:51]2[C:47](=[C:46]([C:3]3[CH:4]=[CH:5][NH:1][N:2]=3)[CH:54]=[CH:53][CH:52]=2)[C:48]2([C:80]3[C:71](=[CH:72][C:73]4[O:78][CH2:77][CH2:76][O:75][C:74]=4[CH:79]=3)[O:70][CH2:69]2)[C:49]1=[O:68]Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 2.46 and making non-critical variations using 1H-pyrazol-3-boronic acid to replace quinolin-3-ylboronic acid, and 4′-bromo-1′-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 4′-bromo-1′-(diphenylmethyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one, 1′-methyl-4′-(1H-pyrazol-3-yl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (63%) as a colorless solid: mp 201-202° C. (dichloromethane/diethyl ether); 1H NMR (300 MHz, CDCl3) δ 7.46-7.35 (m, 2H), 7.25-7.20 (m, 1H), 6.92 (d, J=7.7 Hz, 1H), 6.40 (s, 1H), 6.24 (s, 1H), 5.94 (d, J=2.0 Hz, 1H), 4.74-4.61 (m, 2H), 4.20-4.07 (m, 4H), 3.27 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 178.0, 155.6, 144.7, 144.5, 137.8, 129.2, 128.0, 124.6, 121.6, 111.0, 108.2, 105.5, 99.5, 77.4, 64.5, 63.9, 58.4, 26.9; MS (ES+) m/z 375.9 (M+1).
Sources & evidence
- ORD record
- ord-a796299607554f72a3a5300a3730edda
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916580B2
Reaction notes
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