2-Chloro-8-methylquinoline-3-carboxaldehyde → 8-Methyl-2-(1,3-oxazol-2-yl)quinoline-3-carboxaldehyde

HRID 1948724Notes

Reaction equation

Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:20]1[O:21][CH:22]=[CH:23][N:24]=1)CCC>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:20]1[O:21][CH:22]=[CH:23][N:24]=1)[C:11]([CH:12]=[O:13])=[CH:10]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-chloro-8-methylquinoline-3-carboxaldehyde (250 mg, 1.21 mmol) in DME (3 mL) was added 2-(tributylstannyl)oxazole (0.31 mL, 1.76 mmol) and Pd(PPh3)4 (70 mg, 0.06 mmol). The reaction mixture was heated in a microwave at 100° C. for 45 minutes. More Pd(PPh3)4 (50 mg, 0.04 mmol) was added to the mixture, which was heated at 100° C. for 2 h. Purification by column chromatography (SiO2, 0-100% EtOAc in heptane) gave the title compound as a cream solid (99 mg, 34%). δH (DMSO-d6) 10.85 (s, 1H), 8.91 (s, 1H), 8.52 (d, J 0.6 Hz, 1H), 8.12 (d, J 8.1 Hz, 1H), 7.86 (d, J 7.0 Hz, 1H), 7.64-7.72 (m, 2H), 2.81 (s, 3H). LCMS (ES+) 239 (M+H)+, RT 3.65 minutes (Method 3).

Workup

temperaturewas heated at 100° C. for 2 h
customPurification by column chromatography (SiO2, 0-100% EtOAc in heptane)

Sources & evidence

ORD record: ord-126138a7971c4926b1a5b832c0d89ea1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399483B2

Reaction notes

Loading…