2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178487415, compound

HRID 2271747Notes

Reaction equation

HRID 2271747 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][C@H:18]1[CH2:23][CH2:22][C@H:21]([N:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]1.[CH3:27][O:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[CH:31][C:30]=1[OH:44]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[NH:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([N:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]2)=[CH:3][C:2]([C:33]2[CH:32]=[CH:31][C:30]([OH:44])=[C:29]([O:28][CH3:27])[CH:34]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178484093HCID 178484093, compound

Product 1

HCID 178487415HCID 178487415, compoundYield 31%

Procedure

Following general procedure F, {6-bromo-4-[trans-4-(dimethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone (52 mg, 0.120 mmol) was reacted with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (45 mg, 0.180 mmol) to afford the desired product (17 mg, 31%) as a yellow-green solid: 1H NMR (300 MHz, CD3OD) δ 9.19 (s, 1H), 8.36 (s, 1H), 8.10 (dd, J=8.8, 1.9 Hz, 1H), 7.93 (d, J=8.8 Hz, 1H), 7.30 (d, J=2.1 Hz, 1H), 7.21 (dd, J=8.2, 2.1 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 4.22 (s, 1H), 3.97 (s, 3H), 2.84 (s, 7H), 2.43 (s, 2H), 2.21 (s, 2H), 1.68 (s, 3H), 1.27-1.18 (m, 2H), 1.18-1.07 (m, 2H); ESI MS m/z 460 [C28H33N3O3+H]+; HPLC>99% (AUC), tR=10.86 min.

Sources & evidence

ORD record
ord-dd3b6707993745b4be893e41dc50ee7b
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…