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

HRID 1407920Notes

Reaction equation

HRID 1407920 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.N1C2C(=CC=CC=2)C=C(B(O)O)C=1.Br[C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[C:25]1([C:57]3[C:48](=[CH:49][C:50]4[O:55][CH2:54][CH2:53][O:52][C:51]=4[CH:56]=3)[O:47][CH2:46]1)[C:26](=[O:45])[N:27]2[CH:32](C1C=CC=CC=1)C1C=CC=CC=1>>[O:1]1[CH:5]=[CH:4][C:3]([C:23]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[C:25]2([C:57]4[C:48](=[CH:49][C:50]5[O:55][CH2:54][CH2:53][O:52][C:51]=5[CH:56]=4)[O:47][CH2:46]2)[C:26](=[O:45])[N:27]3[CH3:32])=[CH:2]1

Participants

4

Reactant 3

HCID 2734358Furan-3-boronic acidHCID 2734663Quinoline-3-boronic acidHCID 593525274'-bromo-1'-(diphenylmethyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

Product 1

HCID 461945754'-furan-3-yl-1'-methyl-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 3-furanboronic 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, 4′-furan-3-yl-1′-methyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (65%) as a colorless solid: mp 178-180° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.38-7.29 (m, 2H), 7.00 (d, J=7.9 Hz, 1H), 6.86 (d, J=7.8 Hz, 1H), 6.76 (s, 1H), 6.41 (s, 1H), 6.28 (s, 1H), 6.04-6.01 (m, 1H), 4.68 (d, J=9.0 Hz, 1H), 4.53 (d, J=9.0 Hz, 1H), 4.23-4.09 (m, 4H), 3.26 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 178.0, 155.5, 144.7, 144.3, 142.8, 140.5, 137.9, 130.8, 129.1, 128.1, 125.2, 122.6, 122.5, 111.2, 111.1, 107.4, 99.7, 76.7, 64.6, 64.0, 58.3, 26.8; MS (ES+) m/z 375.9 (M+1).

Sources & evidence

ORD record
ord-f06245eeaaeb4e33ae35415936cb9702
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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