2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 2,6-Dichloro-4-(4-((4-((dimethylamino)methyl)phenyl)amino)-3-(methylsulfonyl)quinolin-6-yl)phenol

HRID 2271795Notes

Reaction equation

HRID 2271795 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=1.[Cl:27][C:28]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[C:30]([Cl:43])[C:29]=1[OH:44]>>[Cl:27][C:28]1[CH:33]=[C:32]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]3[NH:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][N:24]([CH3:25])[CH3:26])=[CH:21][CH:22]=2)[CH:31]=[C:30]([Cl:43])[C:29]=1[OH:44]

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 667152496-bromo-N-(4-((dimethylamino)methyl)phenyl)-3-(methylsulfonyl)quinolin-4-amine

Product 1

HCID 667155332,6-Dichloro-4-(4-((4-((dimethylamino)methyl)phenyl)amino)-3-(methylsulfonyl)quinolin-6-yl)phenolYield 61.4%

Procedure

Following general procedure D, 6-bromo-N-(4-((dimethylamino)methyl)phenyl)-3-(methylsulfonyl)quinolin-4-amine (43 mg, 0.10 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (53 mg, 0.183 mmol) to afford the desired product (31.7 mg, 61%) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 9.00 (s, 1H), 8.06-7.97 (m, 2H), 7.74 (s, 3H), 7.46-7.38 (m, 2H), 7.21 (d, J=8.0 Hz, 2H), 7.13 (s, 2H), 3.86 (s, 2H), 3.27 (s, 3H), 2.45 (s, 6H). ESI MS m/z 516 [C25H23Cl2N3O2S+H]+; HPLC 94.5% (AUC), tR=11.57 min.

Sources & evidence

ORD record
ord-90d997933f2e4b8e8121159e0d1f3320
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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