(6-Methoxypyridin-3-yl)boronic acid → 1'-[(5-chloro-2-thienyl)methyl]-5-(6-methoxypyridin-3-yl)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 1965793Notes

Reaction equation

HRID 1965793 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.CN(C)C1N=CC(B(O)O)=CC=1.Br[C:25]1[CH:26]=[CH:27][C:28]2[O:49][CH2:48][C:31]3([C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]([CH2:40][C:41]4[S:42][C:43]([Cl:46])=[CH:44][CH:45]=4)[C:32]3=[O:47])[C:29]=2[CH:30]=1.BrC1C=CC=C2C=1C1(C3=CC4OCOC=4C=C3OC1)C(=O)N2CC1SC(Cl)=CC=1>>[Cl:46][C:43]1[S:42][C:41]([CH2:40][N:33]2[C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:31]3([C:29]4[CH:30]=[C:25]([C:6]5[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)[CH:26]=[CH:27][C:28]=4[O:49][CH2:48]3)[C:32]2=[O:47])=[CH:45][CH:44]=1

Participants

5

Reactant 4

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 119980755-bromo-1'-[(5-chloro-2-thienyl)methyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneHCID 593525614'-bromo-1'-[(5-chloro-2-thienyl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 593527821'-[(5-chloro-2-thienyl)methyl]-5-(6-methoxypyridin-3-yl)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Procedure

Following the procedure as described in EXAMPLE 16.12 and making non-critical variations using (6-methoxypyridin-3-yl)boronic acid to replace 6-(dimethylamino)pyridin-3-ylboronic acid, and 5-bromo-1′-[(5-chloro-2-thienyl)methyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 4′-bromo-1′-[(5-chloro-2-thienyl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, 1′-[(5-chloro-2-thienyl)methyl]-5-(6-methoxypyridin-3-yl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (20%) as a colorless solid: mp 60-62° C.; 1H NMR (300 MHz, CDCl3) δ 8.16 (d, J=2.5 Hz, 1H), 7.54 (dd, J=8.6, 2.2 Hz, 1H), 7.35 (dd, J=8.4, 1.6 Hz, 1H), 7.27 (t, J=7.7 Hz, 1H), 7.17 (d, J=7.3 Hz, 1H), 7.07-6.98 (m, 2H), 6.95 (d, J=7.8 Hz, 1H), 6.88 (d, J=2.2 Hz, 1H), 6.69 (d, J=8.6 Hz, 1H), 5.12 (d, J=15.8 Hz, 1H), 5.00 (d, J=9.2 Hz, 1H), 4.91 (d, J=15.8 Hz, 1H), 4.73 (d, J=9.2 Hz, 1H), 3.89 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 176.9, 163.2, 160.3, 144.5, 141.3, 137.2, 136.9, 132.2, 131.7, 130.1, 129.8, 129.6, 129.1, 128.5, 126.4, 126.0, 124.1, 123.9, 121.7, 110.9, 110.6, 109.0, 79.7, 60.4, 58.0, 53.5, 39.2; MS (ES+) 475.5 (M+1) 477.5 (M+1).

Sources & evidence

ORD record
ord-322ac28b0a174b5797e4ea84f108958a
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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