Sodium Carbonate → HCID 60198101, compound

HRID 2091554Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[NH:16][CH2:15][CH2:14]2.Br[C:23]1[S:27][C:26]([S:28]([NH:31][CH2:32][CH3:33])(=[O:30])=[O:29])=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>CCCCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:23]2[S:27][C:26]([S:28]([NH:31][CH2:32][CH3:33])(=[O:30])=[O:29])=[CH:25][CH:24]=2)=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:21])[NH:16][CH2:15][CH2:14]2

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of (6-amino-5-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyridin-3-yl)boronic acid (291 mg, 1.02 mmol), 5-bromo-N-ethylthiophene-2-sulfonamide (278 mg, 1.02 mmol), and PdCl2(PPh3)2 (35 mg, 0.05 mmol) in n-BuOH (3 mL) was treated with 2.0 M aq. Na2CO3 solution (1 mL) then microwave heated at 140° C. for 6 min. The reaction was then filtered, and purified by HPLC to provide 5-(6-amino-5-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyridin-3-yl)-N-ethylthiophene-2-sulfonamide as a white solid after preparatory HPLC purification. 1H NMR (300 MHz, MeOH) δ ppm 8.31 (d, J=2.3 Hz, 1H), 8.07 (d, J=8.0 Hz, 1 H), 7.72 (d, J=2.3 Hz, 1H), 7.54 (dd, J=3.8, 2.1 Hz, 1H), 7.52 (d, J=1.7 Hz, 1H), 7.48 (s, 1 H), 7.34 (d, J=3.8 Hz, 1H), 3.57 (dd, J=13.4, 6.5 Hz, 1H), 2.93-3.15 (m, 2H), 1.85-2.03 (m, 3H), 1.13 (dd, J=14.5, 7.2 Hz, 3H); MS (EI) m/z: 429 [M+H]+.

Workup

filtrationThe reaction was then filtered
custompurified by HPLC

Sources & evidence

ORD record: ord-0f9156a01bef43e6950a0b3ee84e4a65
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440652B2

Reaction notes

Loading…