Cesium carbonate → ethyl 5-[4-(6-isopropyloxy-2,4-dimethylpyridin-3-yl)-2-nitrophenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate

HRID 1043954Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:5]=1[C:19]1[N:23]([C@H:24]2[CH2:28][CH2:27][O:26][CH2:25]2)[N:22]=[CH:21][C:20]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30])([O-:3])=[O:2].Br[C:35]1[C:36]([CH3:46])=[N:37][C:38]([O:42][CH:43]([CH3:45])[CH3:44])=[CH:39][C:40]=1[CH3:41].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.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>[CH:43]([O:42][C:38]1[N:37]=[C:36]([CH3:46])[C:35]([C:8]2[CH:7]=[CH:6][C:5]([C:19]3[N:23]([C@H:24]4[CH2:28][CH2:27][O:26][CH2:25]4)[N:22]=[CH:21][C:20]=3[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=2)=[C:40]([CH3:41])[CH:39]=1)([CH3:45])[CH3:44]

Participants

Conditions

Temperature: 110 °C

Procedure

Ethyl 5-[2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate obtained in Preparation Example 7-(2) (70 mg) was dissolved in a mixed solution of 1,4-dioxane (1 mL) and water (0.2 mL), and 3-bromo-6-isopropyloxy-2,4-dimethylpyridine (41.1 mg), Pd(PPh3)4 (17.7 mg) and cesium carbonate (150 mg) were added. The reaction mixture was stirred at 110° C. overnight. After returning the reaction mixture to room temperature, the reaction mixture was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10 to 50% to 100%) to give the title compound (66.5 mg).

Workup

additionwere added
customto room temperature
customthe reaction mixture was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10 to 50% to 100%)

Sources & evidence

ORD record: ord-4968b450c34a47b8a5081013ba9aa7f8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563565B2

Reaction notes

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