Toluene → HCID 58223493, compound

HRID 41281Notes

Reaction equation

C1(C)C=CC=CC=1.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([CH2:16][O:17][CH3:18])[CH:13]=[C:12]([O:19][CH3:20])[C:11]=1[C:21]1[N:22]2[N:28]=[C:27]([O:29][CH3:30])[C:26]([NH:31][CH2:32][CH2:33][CH3:34])=[C:23]2[S:24][CH:25]=1.Br[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.CC(C)([O-])C.[Na+]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([CH2:16][O:17][CH3:18])[CH:13]=[C:12]([O:19][CH3:20])[C:11]=1[C:21]1[N:22]2[N:28]=[C:27]([O:29][CH3:30])[C:26]([N:31]([CH2:32][CH2:33][CH3:34])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[C:23]2[S:24][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a toluene (0.9 mL) solution of 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxy-N-propylpyrazolo[5,1-b][1,3]thiazole-7-amine (70 mg, 0.179 mmol) were added 2-bromopyridine (56.6 mg, 0.358 mmol), sodium tert-butoxide (25.8 mg, 0.269 mmol) and bis(tri-tert-butylphosphine)palladium (4.57 mg, 0.009 mmol), and the mixture was stirred at 100° C. for five hours. After the reaction mixture was returned to room temperature, water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate, and the solvent was distilled off under reduced pressure. The residue was purified by medium pressure amino silica gel column chromatography (n-heptane/ethyl acetate: 10% then 50%) to obtain the title compound (18.2 mg, 0.0388 mmol).

Workup

customwas returned to room temperature
extractionthe reaction mixture was extracted with ethyl acetate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by medium pressure amino silica gel column chromatography (n-heptane/ethyl acetate

Sources & evidence

ORD record: ord-fee7b49b42c44a7d81f434d91c04ba68
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530504B2

Reaction notes

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