2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178464126, compound

HRID 2271741Notes

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]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH2:20][CH2:19]1.[Cl:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[C:32]([O:45][CH3:46])[C:31]=1[OH:47]>>[Cl:29][C:30]1[CH:35]=[C:34]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([CH:14]2[CH2:15][CH2:16]2)=[O:13])=[C:5]3[NH:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([N:24]([CH2:25][CH3:26])[CH2:27][CH3:28])[CH2:20][CH2:19]2)[CH:33]=[C:32]([O:45][CH3:46])[C:31]=1[OH:47]

Participants

Reactant 2

HCID 177502302-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

HCID 178464124HCID 178464124, compound

Product 1

HCID 178464126HCID 178464126, compoundYield 251.6%

Procedure

Following general procedure D, {6-bromo-4-[trans-4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone (31 mg, 0.070 mmol) was reacted with 2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (43 mg, 0.015 mmol) to afford the desired product (19.7 mg, 54%) as an orange-brown solid: 1H NMR (500 MHz, CD3OD) δ 9.15 (s, 1H), 8.34 (d, J=1.8 Hz, 1H), 8.04 (dd, J=8.7, 1.9 Hz, 1H), 7.92 (d, J=8.7 Hz, 1H), 7.31 (d, J=2.1 Hz, 1H), 7.23 (d, J=2.0 Hz, 1H), 4.20 (s, 1H), 3.99 (s, 3H), 3.12 (q, J=7.2 Hz, 4H), 2.89-2.80 (m, 1H), 2.41 (d, J=10.4 Hz, 2H), 2.15 (d, J=9.8 Hz, 2H), 1.82-1.62 (m, 4H), 1.30 (t, J=7.3 Hz, 6H), 1.23-1.16 (m, 2H), 1.15-1.04 (m, 2H); ESI MS m/z 522 [C30H36ClN3O3+H]+; HPLC 98.5% (AUC), tR=11.05 min.

Sources & evidence

ORD record: ord-caa678dcec0e4e1ab3aa2cbfec202914
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

Loading…