1'-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one → 4'-quinolin-3-yl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1H)-one

HRID 1965492Notes

Reaction equation

HRID 1965492 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[C:12]([C:17]4[CH:18]=[N:19][C:20]5[C:25]([CH:26]=4)=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:13]=[CH:14][CH:15]=3)[C:10]3([C:38]4[C:29](=[CH:30][C:31]5[O:36][CH2:35][CH2:34][O:33][C:32]=5[CH:37]=4)[O:28][CH2:27]3)[C:9]2=[O:39])C=CC=CC=1.C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C3(C4C=C(C)C(OC)=CC=4OC3)C2=O)C=CC=CC=1>>[N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[C:17]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[C:10]2([C:38]4[C:29](=[CH:30][C:31]5[O:36][CH2:35][CH2:34][O:33][C:32]=5[CH:37]=4)[O:28][CH2:27]2)[C:9](=[O:39])[NH:8]3)[CH:18]=1

Participants

3

Reactant 2

HCID 593524081'-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 593524521'-(diphenylmethyl)-4'-quinolin-3-yl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

Product 1

HCID 593520724'-quinolin-3-yl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1H)-one

Procedure

Following the procedure as described in EXAMPLE 3 and making non-critical variations using 1′-(diphenylmethyl)-4′-quinolin-3-yl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace 1′-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, 4′-quinolin-3-yl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1H)-one was obtained (99%) as a light yellow solid: mp 221-224° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 10.79 (s, 1H), 8.41 (d, J=2.2 Hz, 1H), 7.96 (d, J=8.3 Hz, 1H), 7.75-7.68 (m, 1H), 7.58-7.53 (m, 2H), 7.40-7.33 (m, 2H), 7.04-7.00 (m, 1H), 6.93-6.88 (m, 1H), 6.36 (s, 1H), 5.84 (s, 1H), 4.42 (d, J=9.5 Hz, 1H), 4.25 (d, J=9.5 Hz, 1H), 4.25-4.05 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 179.0, 155.1, 150.5, 146.9, 144.6, 142.6, 138.3, 136.4, 135.5, 131.8, 130.1, 129.5, 129.1, 128.6, 127.3, 127.0, 124.8, 123.0, 111.2, 110.4, 98.9, 78.27, 64.7, 64.2, 58.4; MS (ES+) m/z 422.8 (M+1).

Sources & evidence

ORD record
ord-15a89eca47a349608db532ce2b8d0451
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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