N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-amine → 6-(2-amino-5-(4-(2-(dimethylamino)propan-2-yl)phenyl)pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 2091594Notes

Reaction equation

HRID 2091594 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][CH:7]=1)([CH3:5])[CH3:4].Br.[NH2:23][C:24]1[C:29]([C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[C:36](=[O:40])[NH:35][CH2:34][CH2:33]3)=[CH:28][C:27](Br)=[CH:26][N:25]=1>>[NH2:23][C:24]1[C:29]([C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[C:36](=[O:40])[NH:35][CH2:34][CH2:33]3)=[CH:28][C:27]([C:9]2[CH:8]=[CH:7][C:6]([C:3]([N:2]([CH3:1])[CH3:21])([CH3:4])[CH3:5])=[CH:11][CH:10]=2)=[CH:26][N:25]=1

Participants

3

Reactant 2

HCID 68736833N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-amineHCID 706547956-(2-amino-5-bromopyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one hydrobromide

Product 1

HCID 601964596-(2-amino-5-(4-(2-(dimethylamino)propan-2-yl)phenyl)pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-oneYield 11.3%

Procedure

General Method C was applied to N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-amine (109 mg, 0.38 mmol) and 6-(2-amino-5-bromopyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one hydrobromide (125 mg, 0.31 mmol) to afford 6-(2-amino-5-(4-(2-(dimethylamino)propan-2-yl)phenyl)pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (14 mg, 11% yield) as a white solid after purification by flash chromatography. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.32 (s, 1H), 7.81-8.11 (m, 2H), 7.37-7.79 (m, 7H), 5.87 (s, 2H), 3.41 (m, 2H), 2.85-3.10 (m, 2H), 2.11 (s, 6H), 1.30 (s, 6 H); MS (EI) m/z=401.5 [M+1]+.

Sources & evidence

ORD record
ord-3c4bb24708144b039122cd120d8dc3b1
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

Loading…