(6-Bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone → Cyclopropyl[4-{4-[(dimethylamino)methyl]piperidin-1-yl}-6-(3-ethoxy-4-hydroxyphenyl)quinolin-3-yl]methanone

HRID 2271727Notes

Reaction equation

HRID 2271727 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]([CH2:23][N:24]([CH3:26])[CH3:25])[CH2:19][CH2:18]1.[CH2:27]([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])[CH3:28]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][N:24]([CH3:25])[CH3:26])[CH2:21][CH2:22]2)=[CH:3][C:2]([C:34]2[CH:33]=[CH:32][C:31]([OH:45])=[C:30]([O:29][CH2:27][CH3:28])[CH:35]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 66715711(6-Bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanoneHCID 680919122-Ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 66715455Cyclopropyl[4-{4-[(dimethylamino)methyl]piperidin-1-yl}-6-(3-ethoxy-4-hydroxyphenyl)quinolin-3-yl]methanoneYield 42%

Procedure

Following general procedure D, (6-bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone (30 mg, 0.072 mmol) was reacted with 2-ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (40 mg, 0.150 mmol) to afford the desired product (14.3 mg, 42%) as a yellow solid: NMR (500 MHz, CD3OD) δ 8.73 (s, 1H), 8.31 (d, J=1.7 Hz, 1H), 8.03 (m, 2H), 7.30 (d, J=2.1 Hz, 1H), 7.22 (dd, J=8.2, 2.1 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 4.22 (q, J=7.0 Hz, 2H), 3.54 (d, J=12.6 Hz, 2H), 3.26-3.12 (m, 2H), 2.59-2.50 (m, 1H), 2.44 (s, 2H), 2.37 (s, 6H), 2.02-1.83 (m, 3H), 1.68-1.53 (m, 2H), 1.49 (t, J=7.0 Hz, 3H), 1.35-1.26 (m, 2H), 1.26-1.15 (m, 2H); ESI MS m/z 474 [C29H35N3O3+H]+; HPLC 96.9% (AUC), tR=10.59 min.

Sources & evidence

ORD record
ord-fadc3e0bbcac491c865c1730aa3cca7b
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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