Hexane → HCID 59394508, compound

HRID 45154Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li][CH2:15]CCC.CCCCCC.C([O:27][C:28](=O)[C:29]([F:32])([F:31])[F:30])C>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[C:11]([C:28]([OH:27])([CH3:15])[C:29]([F:32])([F:31])[F:30])[N:10]([CH3:13])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3-(2,5-dimethyl-pyrrol-1-yl)-1-methyl-1H-pyrazole (1.5 g, 8.6 mmol) in THF (100 mL) at −78° C., 2.5M nBuLi in Hexane (4.1 mL, 10.3 mmol) is added and stirred for 1.5 hours followed by the addition of trifluoro-acetic acid ethyl ester (1.5 g, 10.3 mmol). After 10 min the ice bath is removed and the reaction is allowed to reach room temperature. Then the reaction is cooled down to −78° C. again and methylmagnesium bromide (1.0 M solution in hexane, 8.6 mL) is added. After 5 min the ice bath is removed and the mixture is stirred at room temperature for 3 hour, poured into water, separated, and the water layer is extracted with DCM. The organic layers are combined and concentrated. The residue is purified by FCC to give the title compound. MS (ESI) m/z 288.1 (M+1).

Workup

customAfter 10 min the ice bath is removed
customto reach room temperature
additionmethylmagnesium bromide (1.0 M solution in hexane, 8.6 mL) is added
customAfter 5 min the ice bath is removed
stirringthe mixture is stirred at room temperature for 3 hour
additionpoured into water
customseparated
extractionthe water layer is extracted with DCM
concentrationconcentrated
customThe residue is purified by FCC

Sources & evidence

ORD record: ord-481c7e95d52345e5a01614e6bb39f2fd
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541432B2

Reaction notes

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