2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 68091984, compound

HRID 2271956Notes

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

Participants

Reactant 2

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

HCID 66715828HCID 66715828, compound

Product 1

HCID 68091984HCID 68091984, compoundYield 71.3%

Procedure

Following general procedure F, {6-Bromo-4-[3-(2-(dimethylamino)ethyl)phenylamino]quinolin-3-yl}(cyclopropyl)methanone (58 mg, 0.132 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (57 mg, 0.198 mmol) to afford the desired product (49 mg, 71%) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.46 (s, 1H), 8.22 (dd, J=8.7, 2.0 Hz, 1H), 8.02 (d, J=8.7 Hz, 1H), 7.89 (s, 1H), 7.67-7.59 (m, 1H), 7.56 (d, J=7.7 Hz, 1H), 7.8 (s, 1H), 7.39 (d, J=7.7 Hz, 1H), 7.20 (s, 2H), 3.40-3.34 (m, 2H), 3.19-3.12 (m, 2H), 2.98-2.85 (s, 8H), 1.27-1.16 (m, 4H); ESI MS m/z 520 [C29H27Cl2N3O2+H]+; HPLC 95.9% (AUC), tR=11.40 min.

Sources & evidence

ORD record: ord-58ed1c8578304ad2bf200948761f429e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

Loading…