2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 1-(6-(3,5-dichloro-4-hydroxyphenyl)-4-((1-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)amino)quinolin-3-yl)ethanone

HRID 2271827Notes

Reaction equation

HRID 2271827 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[CH:21]([N:25]([CH3:27])[CH3:26])[CH2:20][CH2:19]2.[Cl:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:31]([Cl:44])[C:30]=1[OH:45]>>[Cl:28][C:29]1[CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[CH:21]([N:25]([CH3:27])[CH3:26])[CH2:20][CH2:19]3)[CH:32]=[C:31]([Cl:44])[C:30]=1[OH:45]

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 667162041-(6-bromo-4-((1-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)amino)quinolin-3-yl)ethanone

Product 1

HCID 680920281-(6-(3,5-dichloro-4-hydroxyphenyl)-4-((1-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)amino)quinolin-3-yl)ethanoneYield 61.3%

Procedure

Following general procedure M, 1-(6-bromo-4-((1-(dimethylamino)-2,3-dihydro-1H-inden-5-yl)amino)quinolin-3-yl)ethanone (19 mg, 0.0448 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (35 mg, 0.12 mmol) to afford the desired product (13.9 mg, 61%) as an orange solid. 1H NMR (500 MHz, DMSO) δ 11.27 (s, 1H), 9.07 (s, 1H), 8.03 (dd, J=8.7, 2.1 Hz, 1H), 7.96-7.87 (m, 2H), 7.35-7.27 (m, 3H), 7.16 (d, J=2.1 Hz, 1H), 7.03-6.97 (m, 1H), 4.45 (br s, 1H), 2.95-2.84 (m, 1H), 2.84-2.73 (m, 1H), 2.65 (s, 3H), 2.21 (s, 6H), 2.14-2.06 (m, 2H). ESI MS m/z 505 [C28H25Cl2N3O2+H]+; HPLC 98.5% (AUC), tR=11.22 min.

Sources & evidence

ORD record
ord-50ad7d546bbb48f08f443dbbf3d95d7d
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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