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

HRID 1407915Notes

Reaction equation

HRID 1407915 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.N1C2C(=CC=CC=2)C=C(B(O)O)C=1.Br[C:26]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:27]=1[C:28]1([C:54]3[C:45](=[CH:46][C:47]4[O:52][CH2:51][CH2:50][O:49][C:48]=4[CH:53]=3)[O:44][CH2:43]1)[C:29](=[O:42])[N:30]2[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.BrC1C=CC=C2C=1C1(C3C(=CC4OCCOC=4C=3)OC1)C(=O)N2C(C1C=CC=CC=1)C1C=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:26]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:27]=2[C:28]2([C:54]4=[CH:53][C:48]5[O:49][CH2:50][CH2:51][O:52][C:47]=5[CH:46]=[C:45]4[O:44][CH2:43]2)[C:29](=[O:42])[N:30]3[CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 201262(4-Methoxyphenyl)boronic acidHCID 2734663Quinoline-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 593521654'-(4-methoxyphenyl)-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 4-methoxyphenyl 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′-(4-methoxyphenyl)-1′-(pyridin-2-ylmethyl)-3,7-dihydro-2H-spiro[benzofuro[5,6-b][1,4]dioxine-8,3′-indolin]-2′-one was obtained (68%) as a colorless solid: mp 205-206° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.59 (d, J=4.7 Hz, 1H), 7.65-7.68 (m, 1H), 7.32-7.17 (m, 3H), 6.91-6.84 (m, 2H), 6.78-6.61 (m, 4H), 6.41 (s, 1H), 6.25 (s, 1H), 5.26 (d, J=15.8 Hz, 1H), 4.92 (d, J=15.8 Hz, 1H), 4.68 (d, J=9.0 Hz, 1H), 4.36 (d, J=9.0 Hz, 1H), 4.27-4.08 (m, 4H), 3.77 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 178.3, 158.9, 155.6, 155.5, 149.5, 144.6, 142.6, 140.0, 137.9, 137.1, 130.9, 129.8, 129.0, 128.7, 125.7, 122.9, 122.8, 121.7, 113.2, 111.1, 108.5, 99.4, 64.6, 64.0, 58.5, 55.3, 46.2; MS (ES+) m/z 493.0 (M+1).

Sources & evidence

ORD record
ord-862ec1133ed44ac59df20be3b7dcc1a0
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…