Sodium ethanethiolate → 2-(7-(2-Methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-4-(oxazol-5-yl)quinolin-8-ol

HRID 1095699Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[N:17]3[CH:18]=[CH:19][C:20]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:21][C:16]3=[N:15][CH:14]=1)[CH:9]=[C:8]2[C:27]1[O:31][CH:30]=[N:29][CH:28]=1.C([S-])C.[Na+]>CN(C=O)C>[CH3:26][O:25][CH2:24][CH2:23][O:22][C:20]1[CH:19]=[CH:18][N:17]2[C:13]([C:10]3[CH:9]=[C:8]([C:27]4[O:31][CH:30]=[N:29][CH:28]=4)[C:7]4[C:12](=[C:3]([OH:2])[CH:4]=[CH:5][CH:6]=4)[N:11]=3)=[CH:14][N:15]=[C:16]2[CH:21]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To 5-(8-methoxy-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-4-yl)oxazole (80 mg, 0.19 mmol) in DMF (3 mL) was added sodium ethanethiolate (162 mg, 1.9 mmol). The reaction vial was sealed and heated to 150° C. for 2 hours. The reaction was then cooled to ambient temperature and concentrated. The residue was purified by flash column chromatography (DCM/MeOH 10:1) providing the desired product (39%).

Workup

customThe reaction
customvial was sealed
temperatureThe reaction was then cooled to ambient temperature
concentrationconcentrated
customThe residue was purified by flash column chromatography (DCM/MeOH 10:1)

Sources & evidence

ORD record: ord-273bc1942962477fa777aaa4a5af44fa
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

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