HCID 18187614, compound → HCID 66577688, compound

HRID 1624432Notes

Reaction equation

[CH2:1]([C:8]1[CH:9]=[N:10][CH:11]=[C:12](Br)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.C([Li])CCC.[Br:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:36][N:35]=[C:34]([CH3:37])[C:33]=2[CH:38]=[O:39])=[CH:28][CH:27]=1>C1COCC1>[CH2:1]([C:8]1[CH:13]=[C:12]([CH:38]([C:33]2[C:34]([CH3:37])=[N:35][O:36][C:32]=2[C:29]2[CH:30]=[CH:31][C:26]([Br:25])=[CH:27][CH:28]=2)[OH:39])[CH:11]=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-Benzyl-5-bromo-pyridine (0.474 g, 1.91 mmol) was dissolved in THF (10 mL) and cooled to 0° C. Isopropylmagnesium chloride (2 M in THF, 0.96 mL, 1.91 mmol) was added dropwise and the reaction was allowed to warm to room temperature and stirred for 1 hour. Analytical LCMS indicated no reaction so an additional portion of isopropylmagnesium chloride (1.91 mmol) was added and the reaction stirred for 1 hour at room temperature. Analytical LCMS still indicated no progress so the reaction was cooled to −78° C. and n-butyllithium (2.5 M in hexanes, 0.764 mL, 1.91 mL) was added. The reaction was allowed to slowly warm to 0° C. then 5-(4-bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (0.610 g, 2.29 mmol) was added and the reaction was allowed to warm to room temperature. The reaction was quenched with H2O, submitted to standard aqueous workup and then purified via silica gel chromatography to yield the title compound.

Workup

temperatureto warm to room temperature
additionwas added
stirringthe reaction stirred for 1 hour at room temperature
temperaturewas cooled to −78° C.
temperatureto slowly warm to 0° C.
temperatureto warm to room temperature
customThe reaction was quenched with H2O
custompurified via silica gel chromatography

Sources & evidence

ORD record: ord-896a1b67814e4ab99fd92a02b8fe2072
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778983B2

Reaction notes

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