Diisopropylethylamine → 1-((4-Bromopyridin-2-yl)amino)-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

HRID 1399900Notes

Reaction equation

[NH2:1][CH2:2][CH:3]([OH:15])[CH2:4][N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1.[Br:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19](F)[CH:18]=1.CCN(C(C)C)C(C)C>CC(O)C>[Br:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH:1][CH2:2][CH:3]([OH:15])[CH2:4][N:5]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6]2)[CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (14.0 g, 67.9 mmol), 4-bromo-2-fluoropyridine (10.0 g, 56.8 mmol) and DIPEA (11.0 g, 85.3 mmol) in i-PrOH (35 mL) were combined in a sealed tube and stirred at 100° C. for 26 h. The reaction mixture was then concentrated and the residue purified by column chromatography to give the desired product (12.0 g, 58.5%). LCMS (m/z): 362.0/364.0 [M+H]+/[M+2+H]+

Workup

customwere combined in a sealed tube
concentrationThe reaction mixture was then concentrated
customthe residue purified by column chromatography

Sources & evidence

ORD record: ord-7e766446b1fd4a2480e454b69b8086f3
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906900B2

Reaction notes

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