Triphenylphosphine → HCID 86688730, compound

HRID 1527956Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=2[OH:20])[N:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O[C:43](=O)[C:44]([CH2:48][CH3:49])([CH3:47])[CH2:45][CH3:46])C>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:43][C:44]([CH2:48][CH3:49])([CH3:47])[CH2:45][CH3:46])[N:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-(5-bromo-2-hydroxy-benzyl)-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester, 6 (0.20 g, 0.60 mmol), triphenylphosphine (0.31 g, 1.2 mmol), ditert-butylazodicarboxylate (0.27 g, 1.2 mmol) and 2-ethyl-2-methyl-butan-1-ol 20 (0.13 g, 1.2 mmol) in a mixture of THF (8 mL) was heated at 100° C. in an Emrys microwave reactor for 20 minutes. The volatiles were removed in vacuo and the crude product was purified on silica to yield 1-[5-bromo-2-(2-ethyl-2-methyl-butoxy)-benzyl]-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester, 22.

Workup

customThe volatiles were removed in vacuo
customthe crude product was purified on silica

Sources & evidence

ORD record: ord-8498d1f1fbd5422dad29e390cae18559
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090566B2

Reaction notes

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