1,4-Dioxane → tert-Butyl{3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-ethyl-6-methoxymethylpyrazolo[5,1-b][1,3]thiazol-7-yl}carbamate

HRID 41274Notes

Reaction equation

O1[CH2:6][CH2:5][O:4][CH2:3]C1.[C:7]([O:11][C:12](=[O:38])[NH:13][C:14]1C(OC)=[N:16][N:17]2[C:21]([C:22]3[C:27]([O:28][CH3:29])=[CH:26][C:25]([CH2:30][O:31][CH3:32])=[CH:24][C:23]=3[O:33][CH3:34])=[C:20](Br)[S:19][C:18]=12)([CH3:10])([CH3:9])[CH3:8].[CH2:39]([Zn]CC)[CH3:40]>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.CCCCCCC.C(OCC)(=O)C>[C:7]([O:11][C:12](=[O:38])[NH:13][C:14]1[C:6]([CH2:5][O:4][CH3:3])=[N:16][N:17]2[C:21]([C:22]3[C:23]([O:33][CH3:34])=[CH:24][C:25]([CH2:30][O:31][CH3:32])=[CH:26][C:27]=3[O:28][CH3:29])=[C:20]([CH2:39][CH3:40])[S:19][C:18]=12)([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To a dioxane (5 mL) solution of tert-butyl{2-bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}carbamate (118 mg, 0.224 mmol), 1M diethyl zinc (0.448 mL, 0.448 mmol) and bis(tri-tert-butylphosphine)palladium(0) (5.70 mg, 0.011 mmol) were added, and the mixture was heated at 60° C. for one hour. After the reaction was completed, the solvent was directly distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=1/1) to obtain the title compound (84 mg, 0.176 mmol).

Workup

distillationthe solvent was directly distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

Sources & evidence

ORD record: ord-d3ce3cfeb8994b038d83d377dfc543e2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530504B2

Reaction notes

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