2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 2-Chloro-4-[4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}-3-(methylsulfonyl)quinolin-6-yl]-6-methoxyphenol

HRID 2271770Notes

Reaction equation

HRID 2271770 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[N:16]1[CH2:21][CH2:20][CH:19]([CH:22]([N:24]([CH3:26])[CH3:25])[CH3:23])[CH2:18][CH2:17]1.[Cl:27][C:28]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[C:30]([O:43][CH3:44])[C:29]=1[OH:45]>>[Cl:27][C:28]1[CH:33]=[C:32]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:13])=[O:14])=[C:5]3[N:16]2[CH2:17][CH2:18][CH:19]([CH:22]([N:24]([CH3:26])[CH3:25])[CH3:23])[CH2:20][CH2:21]2)[CH:31]=[C:30]([O:43][CH3:44])[C:29]=1[OH:45]

Participants

3

Reactant 2

HCID 177502302-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 667152671-{1-[6-Bromo-3-(methylsulfonyl)quinolin-4-yl]piperidin-4-yl}-N,N-dimethylethanamine

Product 1

HCID 866929332-Chloro-4-[4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}-3-(methylsulfonyl)quinolin-6-yl]-6-methoxyphenolYield 55.2%

Procedure

Following general procedure D, 1-{1-[6-bromo-3-(methylsulfonyl)quinolin-4-yl]piperidin-4-yl}-N,N-dimethylethanamine (35 mg, 0.079 mmol) was reacted with 2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (43 mg, 0.150 mmol) to afford the desired product (22.6 mg, 55%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.22 (s, 1H), 8.41 (s, 1H), 8.20-8.15 (m, 2H), 7.33 (d, J=2.1 Hz, 1H), 7.25 (d, J=2.1 Hz, 1H), 4.00 (s, 3H), 3.71 (t, J=11.8 Hz, 2H), 3.56 (d, J=11.9 Hz, 2H), 3.49-3.42 (m, 3H), 2.96 (s, 1H), 2.64 (s, 6H), 2.10-1.90 (m, 3H), 1.82-1.63 (m, 2H), 1.26 (d, J=6.7 Hz, 3H); ESI MS m/z 518 [C26H32ClN3O4S+H]+; HPLC 98.8% (AUC), tR=10.97 min.

Sources & evidence

ORD record
ord-210d21d3efc44ee89d02ca15659c0f15
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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