2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 68091941, compound

HRID 2271814Notes

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:16])[CH2:13][CH2:14][CH3:15])=[C:5]2[NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1.[Cl:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:31]([Cl:44])[C:30]=1[OH:45]>>[Cl:28][C:29]1[CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:16])[CH2:13][CH2:14][CH3:15])=[C:5]3[NH:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH3:26])[CH3:27])=[CH:20][CH:19]=2)[CH:32]=[C:31]([Cl:44])[C:30]=1[OH:45]

Participants

Reactant 2

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

HCID 68091756HCID 68091756, compound

Product 1

HCID 68091941HCID 68091941, compoundYield 43%

Procedure

Following general procedure D, 1-(6-bromo-4-((4-((dimethylamino)methyl)phenyl)amino)quinolin-3-yl)butan-1-one (43 mg, 0.10 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (47 mg, 0.16 mmol) to afford the desired product (21.8 mg, 43%) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 9.12 (s, 1H), 7.97-7.87 (m, 2H), 7.73 (d, J=1.8 Hz, 1H), 7.46-7.39 (m, 2H), 7.26-7.19 (m, 2H), 7.10 (s, 2H), 3.80 (s, 2H), 3.17 (t, J=7.3 Hz, 2H), 2.39 (s, 6H), 1.81 (h, J=7.4 Hz, 2H), 1.05 (t, J=7.4 Hz, 3H). ESI MS m/z 508 [C28H27Cl2N3O2+H]+; HPLC 99% (AUC), tR=11.22 min.

Sources & evidence

ORD record: ord-40ed4e50592747f69fb60dc53f519c93
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

Loading…