2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → Cyclopropyl{4-[4-(diethylamino)cyclohexylamino]-6-(4-hydroxy-3-methoxyphenyl)quinolin-3-yl}methanone

HRID 2271739Notes

Reaction equation

HRID 2271739 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]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][CH:18]1[CH2:23][CH2:22][CH:21]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH2:20][CH2:19]1.[CH3:29][O:30][C:31]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=[CH:33][C:32]=1[OH:46]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[NH:17][CH:18]2[CH2:19][CH2:20][CH:21]([N:24]([CH2:25][CH3:26])[CH2:27][CH3:28])[CH2:22][CH2:23]2)=[CH:3][C:2]([C:35]2[CH:34]=[CH:33][C:32]([OH:46])=[C:31]([O:30][CH3:29])[CH:36]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 66716442{6-Bromo-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone

Product 1

HCID 66715298Cyclopropyl{4-[4-(diethylamino)cyclohexylamino]-6-(4-hydroxy-3-methoxyphenyl)quinolin-3-yl}methanoneYield 63.1%

Procedure

Following general procedure F, {6-bromo-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone (58 mg, 0.130 mmol) was reacted with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (34 mg, 0.136 mmol) to afford the desired product (40 mg, 60%) as a yellow glass: 1H NMR (300 MHz, CD3OD) δ 9.26 (s, 0.5H), 9.17 (s, 0.5H), 8.33 (dd, J=8.2, 1.6 Hz, 1H), 8.09 (dt, J=8.8, 1.7 Hz, 1H), 7.90 (d, J=8.7 Hz, 1H), 7.25 (dd, J=12.8, 2.1 Hz, 1H), 7.21-7.08 (m, 1H), 6.99-6.87 (m, 1H), 4.81 (s, 1H), 3.96 (d, J=3.5 Hz, 3H), 3.64-3.44 (m, 1H), 3.40-3.12 (m, 3H), 2.96-2.76 (m, 1H), 2.41 (s, 1H), 2.24 (d, J=12.4 Hz, 2H), 2.14-1.83 (m, 4H), 1.73 (t, J=9.7 Hz, 2H), 1.46-1.30 (m, 6H), 1.26-1.07 (m, 4H); ESI MS m/z 488 [C30H37N3O3+H]+; HPLC 98.9% (AUC), tR=6.24 min.

Sources & evidence

ORD record
ord-00e03dd0542d43b9bd22fb880d7db9a3
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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