2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 1-(6-(3-Chloro-5-fluoro-4-hydroxyphenyl)-4-((4-((dimethylamino)methyl)phenyl)amino)quinolin-3-yl)propan-1-one

HRID 2271790Notes

Reaction equation

HRID 2271790 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:15])[CH2:13][CH3:14])=[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]([F: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]([C:12](=[O:15])[CH2:13][CH3:14])=[C:5]3[NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH3:25])[CH3:26])=[CH:19][CH:18]=2)[CH:31]=[C:30]([F:43])[C:29]=1[OH:44]

Participants

3

Reactant 2

HCID 667160792-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 680921371-(6-Bromo-4-((4-((dimethylamino)methyl)phenyl)amino)quinolin-3-yl)propan-1-one

Product 1

HCID 866929431-(6-(3-Chloro-5-fluoro-4-hydroxyphenyl)-4-((4-((dimethylamino)methyl)phenyl)amino)quinolin-3-yl)propan-1-oneYield 62.1%

Procedure

Following general procedure M, 1-(6-bromo-4-((4-((dimethylamino)methyl)phenyl)amino)quinolin-3-yl)propan-1-one (125 mg, 0.30 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (91 mg, 0.33 mmol) to afford the desired product (89 mg, 62%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 11.00 (s, 1H), 9.02 (s, 1H), 8.09-7.88 (m, 3H), 7.35-7.18 (m, 4H), 7.16-7.09 (m, 2H), 3.42 (s, 2H), 3.09 (q, J=7.1 Hz, 2H), 2.14 (s, 6H), 0.98 (t, J=7.1 Hz, 3H). APCI MS m/z 478 [C27H25ClFN3O2+H]+; HPLC>99% (AUC), tR=8.10 min.

Sources & evidence

ORD record
ord-a437500a341f4fc7a13c20a5de675d0a
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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