2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178467082, compound

HRID 2271793Notes

Reaction equation

HRID 2271793 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@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:18][CH2:17]1.[Cl:26][C:27]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[C:29]([Cl:42])[C:28]=1[OH:43]>>[Cl:26][C:27]1[CH:32]=[C:31]([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@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][N:23]([CH3:24])[CH3:25])[CH2:18][CH2:17]2)[CH:30]=[C:29]([Cl:42])[C:28]=1[OH:43]

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178467068HCID 178467068, compound

Product 1

HCID 178467082HCID 178467082, compoundYield 64%

Procedure

Following general procedure D, 1-(6-bromo-4-((trans-4-((dimethylamino)methyl)cyclohexyl)amino)quinolin-3-yl)ethanone (32 mg, 0.079 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (51 mg, 0.176 mmol) to afford the desired product (24.5 mg, 64%) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 8.93 (s, 1H), 8.34 (d, J=2.0 Hz, 2H), 7.99 (dd, J=8.7, 2.0 Hz, 1H), 7.89 (d, J=8.7 Hz, 1H), 7.62 (s, 2H), 4.27-4.20 (m, 1H), 2.80-2.74 (d, J=6.9 Hz, 2H), 2.71-2.63 (m, 9H), 2.37 (d, J=12.8 Hz, 2H), 1.99 (d, J=13.2 Hz, 2H), 1.89-1.85 (m, 1H), 1.70-1.58 (m, 2H), 1.33-1.21 (m, 2H). ESI MS m/z 486 [C26H29Cl2N3O2+H]+; HPLC 97.9% (AUC), tR=10.81 min.

Sources & evidence

ORD record
ord-e0c80c80122549039eb30c79fae06383
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…