Quinoline-3-boronic acid → 4'-(6-(dimethylamino)pyridin-3-yl)-1'-(pyridin-2-ylmethyl)-3,7-dihydro-2H-spiro[benzofuro[5,6-b][1,4]dioxine-8,3'-indolin]-2'-one

HRID 1407914Notes

Reaction equation

HRID 1407914 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][N:4]=1.N1C2C(=CC=CC=2)C=C(B(O)O)C=1.Br[C:27]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:28]=1[C:29]1([C:55]3[C:46](=[CH:47][C:48]4[O:53][CH2:52][CH2:51][O:50][C:49]=4[CH:54]=3)[O:45][CH2:44]1)[C:30](=[O:43])[N:31]2[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1.BrC1C=CC=C2C=1C1(C3C(=CC4OCCOC=4C=3)OC1)C(=O)N2C(C1C=CC=CC=1)C1C=CC=CC=1>>[CH3:1][N:2]([CH3:12])[C:3]1[N:4]=[CH:5][C:6]([C:27]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:28]=2[C:29]2([C:55]4=[CH:54][C:49]5[O:50][CH2:51][CH2:52][O:53][C:48]=5[CH:47]=[C:46]4[O:45][CH2:44]2)[C:30](=[O:43])[N:31]3[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 2734663Quinoline-3-boronic acidHCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 593522974'-bromo-1'-(pyridin-2-ylmethyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-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 593527534'-(6-(dimethylamino)pyridin-3-yl)-1'-(pyridin-2-ylmethyl)-3,7-dihydro-2H-spiro[benzofuro[5,6-b][1,4]dioxine-8,3'-indolin]-2'-one

Procedure

Following the procedure as described in EXAMPLE 2.46 and making non-critical variations using 2-(dimethylamino)pyridine-5-boronic acid to replace quinolin-3-ylboronic acid, and 4′-bromo-1′-(pyridin-2-ylmethyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-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′-(6-(dimethylamino)pyridin-3-yl)-1′-(pyridin-2-ylmethyl)-3,7-dihydro-2H-spiro[benzofuro[5,6-b][1,4]dioxine-8,3′-indolin]-2′-one was obtained (44%) as a colorless solid: mp 187-188° C. (methanol/dichloromethane); 1H NMR (300 MHz, CDCl3) δ 8.61-8.56 (m, 1H), 7.80-7.77 (m, 1H), 7.70-7.62 (m, 1H), 7.32-7.17 (m, 3H), 6.91-6.81 (m, 2H), 6.66 (dd, J=8.8, 2.5 Hz, 1H), 6.40 (s, 1H), 6.27 (s, 1H), 6.21 (d, J=8.8 Hz, 1H), 5.25 (d, J=15.8 Hz, 1H), 4.93 (d, J=15.8 Hz, 1H), 4.71 (d, J=9.0 Hz, 1H), 4.46 (d, J=9.0 Hz, 1H), 4.30-4.08 (m, 4H), 3.05 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 178.2, 158.5, 155.6, 155.4, 149.5, 147.4, 144.7, 142.7, 138.0, 137.6, 137.2, 137.1, 129.5, 128.8, 125.9, 122.8, 122.7, 122.0, 121.7, 111.2, 108.6, 104.3, 99.4, 64.6, 64.0, 58.4, 46.2, 38.1; MS (ES+) m/z 507.0 (M+1).

Sources & evidence

ORD record
ord-6ce4656478424e91b4acf20c8daf0695
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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