Quinoline-3-boronic acid → 1'-methyl-4'-(1-methyl-1H-pyrazol-4-yl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

HRID 2385539Notes

Reaction equation

HRID 2385539 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]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:53]1[CH:61]=[CH:60][CH:59]=[C:58]2[C:54]=1[C:55]1([C:87]3[C:78](=[CH:79][C:80]4[O:85][CH2:84][CH2:83][O:82][C:81]=4[CH:86]=3)[O:77][CH2:76]1)[C:56](=[O:75])[N:57]2[CH:62](C1C=CC=CC=1)C1C=CC=CC=1>>[CH3:62][N:57]1[C:58]2[C:54](=[C:53]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:61]=[CH:60][CH:59]=2)[C:55]2([C:87]3[C:78](=[CH:79][C:80]4[O:85][CH2:84][CH2:83][O:82][C:81]=4[CH:86]=3)[O:77][CH2:76]2)[C:56]1=[O:75]

Participants

5

Reactant 4

HCID 2734663Quinoline-3-boronic acidHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 592634674'-bromo-1'-methylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 593525274'-bromo-1'-(diphenylmethyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

Product 1

HCID 593521271'-methyl-4'-(1-methyl-1H-pyrazol-4-yl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

Procedure

Following the procedure as described in EXAMPLE 2.46 and making non-critical variations using 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 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′-(1-methyl-1H-pyrazol-4-yl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (58%) as a colorless solid: mp 220-222° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) 7.32 (dd, J=7.9, 7.9 Hz, 1H), 7.16 (s, 1H), 6.99 (d, J=7.8 Hz, 1H), 6.83 (d, J=7.8 Hz, 1H), 6.53 (s, 1H), 6.42 (s, 1H), 6.31 (s, 1H), 4.66 (d, J=9.1 Hz, 1H), 4.48 (d, J=9.1 Hz, 1H), 4.23-4.09 (m, 4H), 3.75 (s, 3H), 3.25 (s, 3H); 130 NMR (75 MHz, CDCl3) δ 178.0, 155.6, 144.8, 144.2, 138.7, 138.0, 130.8, 129.3, 129.1, 127.8, 125.2, 122.7, 119.0, 111.5, 107.0, 99.4, 76.7, 64.6, 64.0, 58.3, 38.9, 26.8; MS (ES+) m/z 390.0 (M+1).

Sources & evidence

ORD record
ord-f1c3464a180c469dbbcceede7fd4e33a
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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