(6-Methoxypyridin-3-yl)boronic acid → HCID 11998074, compound

HRID 425646Notes

Reaction equation

HRID 425646 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([C:25]3=[CH:26][C:27]4[O:31][CH2:30][O:29][C:28]=4[CH:32]=[C:24]3[O:23][CH2:22]1)[C:5](=[O:21])[N:6]2[CH2:11][C:12]1[O:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=1.BrC1C=CC=[C:39]2[C:35]=1[C:36]1([C:52]3=CC4OCOC=4C=[C:51]3[O:50][CH2:49]1)C(=O)[N:38]2CCCCC.COC1N=CC(B(O)O)=CC=1.CN(C)C1N=CC(B(O)O)=CC=1>>[CH3:49][O:50][C:51]1[N:38]=[CH:39][C:35]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[C:4]2([C:25]4=[CH:26][C:27]5[O:31][CH2:30][O:29][C:28]=5[CH:32]=[C:24]4[O:23][CH2:22]2)[C:5](=[O:21])[N:6]3[CH2:11][C:12]2[O:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)=[CH:36][CH:52]=1

Participants

5

Reactant 4

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 592633394'-bromo-1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)oneHCID 59263391HCID 59263391, compound

Product 1

HCID 11998074HCID 11998074, compound

Procedure

Following the procedure as described in EXAMPLE 4, and making non-critical variations using 4′-bromo-1′-{[5-(trifluoromethyl)-2-furyl]methyl}spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 4′-bromo-1′-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and (6-methoxypyridin-3-yl)boronic acid to replace [6-(dimethylamino)pyridin-3-yl]boronic acid, the title compound was obtained (51%) as a colorless solid: mp 174-176° C.; 1H NMR (300 MHz, CDCl3) δ 7.73 (d, 1H), 7.69 (d, 1H), 7.34 (t, 1H), 7.03 (d, 1H), 6.89-6.86 (m, 2H), 6.65 (d, 1H), 6.61 (d, 1H), 6.56 (d, 1H), 6.17 (d, 2H), 5.87 (d, 2H), 4.99 (ABq, 2H), 4.56 (ABq, 2H), 3.90 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 177.7, 163.5, 158.4, 156.1, 151.8, 151.8, 149.2, 147.8, 146.1, 142.3, 141.6, 138.8, 136.9, 132.6, 130.0, 129.1, 127.8, 127.2, 126.2, 119.9, 112.7, 112.7, 110.9, 109.6, 109.5, 108.5, 102.3, 101.6, 93.6, 78.2, 58.5, 53.6, 37.0; MS (ES+) m/z 537.4 (M+1).

Sources & evidence

ORD record
ord-25c0816005ce460c8ae2ccf992a830ff
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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