Triphenylphosphine → HCID 178472394, compound

HRID 626330Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.O[C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C@@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1)[N:6]=[CH:5]2

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 5-bromoindazole (5.00 g), ethyl trans-4-hydroxycyclohexanecarboxylate (8.73 g), triphenylphosphine (13.3 g) in THF (150 mL) was stirred at 0° C. for 15 minutes. To the reaction solution was added dropwise diethylazodicarboxylate (9.03 g) under nitrogen atmosphere at 0° C., and the mixture was stirred at 50° C. for 13 hours. Then, the solvent was removed out, and ethyl acetate (100 mL) and petroleum ether (30 mL) were added thereto. The mixture was stirred at room temperature for 2 hours. The reaction solution was filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:80-1:15 as the eluting solvent) to give Compound Q14 (3.50 g).

Workup

customThen, the solvent was removed out
additionethyl acetate (100 mL) and petroleum ether (30 mL) were added
stirringThe mixture was stirred at room temperature for 2 hours
filtrationThe reaction solution was filtered
customthe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate
custompetroleum ether=1:80-1:15 as the eluting solvent) to give Compound Q14 (3.50 g)

Sources & evidence

ORD record: ord-da0e3f3795c4481e9e82213e5cadc299
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309221B2

Reaction notes

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