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

HRID 2271729Notes

Reaction equation

HRID 2271729 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[N:17]1[CH2:22][CH2:21][CH:20]([CH:23]([N:25]([CH3:27])[CH3:26])[CH3:24])[CH2:19][CH2:18]1.[CH3:28][O:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][C:31]=1[OH:45]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[N:17]2[CH2:22][CH2:21][CH:20]([CH:23]([N:25]([CH3:27])[CH3:26])[CH3:24])[CH2:19][CH2:18]2)=[CH:3][C:2]([C:34]2[CH:33]=[CH:32][C:31]([OH:45])=[C:30]([O:29][CH3:28])[CH:35]=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 86692863(6-Bromo-4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 86692923Cyclopropyl(4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}-6-(4-hydroxy-3-methoxyphenyl)quinolin-3-yl)methanoneYield 56.6%

Procedure

Following general procedure F, (6-bromo-4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone (42 mg, 0.097 mmol) was reacted with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (36 mL, 0.146 mmol) to afford the desired product (26 mg, 56%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 8.82 (s, 1H), 8.29 (d, J=1.6 Hz, 1H), 8.19-7.97 (m, 2H), 7.31 (d, J=2.1 Hz, 1H), 7.23 (dd, J=8.2, 2.1 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 3.98 (s, 3H), 3.61 (t, J=12.8 Hz, 2H), 3.48-3.36 (m, 1H), 3.27-3.17 (m, 2H), 2.98-2.84 (m, 5H), 2.67-2.56 (m, 1H), 2.11-1.73 (m, 5H), 1.40 (d, J=6.8 Hz, 3H), 1.34-1.23 (m, 6H); ESI MS m/z 474 [C29H35N3O3+H]+; HPLC 98.6% (AUC), tR=9.95 min.

Sources & evidence

ORD record
ord-7e8fdd474de74890b332729a0a47b200
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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