Tri-o-tolylphosphine → HCID 59128683, compound

HRID 1991119Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N:11]3[C:19](=[O:20])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])[CH:9]=2)[N:4]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:3]=1.C[Sn](C)(C)[C:33]1[S:37][CH:36]=[N:35][CH:34]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[OH2:62].CC#N>C1(C)C=CC=CC=1.CC#N.CC#N.Cl[Pd]Cl>[C:25]1([S:22]([N:4]2[C:5]3=[N:6][CH:7]=[C:8]([NH:11][C:12]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19]([OH:20])=[O:62])=[O:21])[CH:9]=[C:10]3[C:2]([C:33]3[S:37][CH:36]=[N:35][CH:34]=3)=[CH:3]2)(=[O:23])=[O:24])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of bromide 43 (50 mg, 0.104 mmol), 5-(trimethylstannyl)thiazole (51.1 mg, 0.21 mmol), PdCl2(MeCN)2 (2.67 mg, 10 μmol), and P(o-tolyl)3 (6.27 mg, 21 μmol) in toluene (5 mL) was heated in darkness at 85° C. overnight and then refluxed for 2 d. The mixture was concentrated and the product isolated by LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—MeCN (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 44 (20 mg, 38%). 1H NMR (400 MHz; CDCl3+3 drops of CD3OD) δ 7.30 (dd, J=4.5, 2.0 Hz, 2H), 7.35 (t, J=7.4 Hz, 2H), 7.44-7.50 (m, 2H), 7.61-7.63 (m, 1H), 7.80 (s, 1H), 7.98 (d, J=1.4 Hz, 1H), 8.00 (s, 2H), 8.42 (d, J=2.3 Hz, 1H), 8.59 (d, J=2.3 Hz, 1H), 8.70 (s, 1H). MS (ES) m/z 505 (MH+).

Workup

temperaturerefluxed for 2 d
concentrationThe mixture was concentrated
customthe product isolated by LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record: ord-1227fada15524311a4e7961efe1be548
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645769B2

Reaction notes

Loading…