Tributyltin Chloride → HCID 71143890, compound

HRID 2173032Notes

Reaction equation

[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[CH:4]=[N:3]1.C([Li])CCC.[CH2:15]([Sn:19]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])Cl)[CH2:16][CH2:17][CH3:18]>C1COCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([Sn:19]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:15][CH2:16][CH2:17][CH3:18])[S:9][C:5]=2[CH:4]=[N:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a cold (−78° C.) mixture of 1-methyl-1H-thieno[3,2-c]pyrazole (200 mg, 1.447 mmol) in THF (10 mL) was added n-butyllithium (0.637 mL, 1.592 mmol) dropwise under a nitrogen atmosphere. The reaction mixture was stirred at −78° C. for 60 minutes. Tributylchlorostannane (0.471 mL, 1.737 mmol) was added, and the reaction mixture was stirred at −78° C. for 60 minutes and then warmed to room temperature over a period of 2 hours. The reaction was quenched with brine (20 mL) and extracted with ethyl acetate (2×30 mL). The organic layers were combined, dried over sodium sulfate, concentrated, and purified via flash chromatography, eluting with 20% EtOAc and hexane to give the title compound as a clear oil (420 mg, 68%). 1H NMR (400 MHz, CDCl3) δ ppm 0.76-0.99 (m, 9H), 0.99-1.22 (m, 6H), 1.22-1.51 (m, 6H), 1.51-1.72 (m, 6H), 4.02 (s, 3H), 6.87 (d, J=0.51 Hz, 1H), 7.58 (s, 1H).

Workup

stirringthe reaction mixture was stirred at −78° C. for 60 minutes
temperaturewarmed to room temperature over a period of 2 hours
customThe reaction was quenched with brine (20 mL)
extractionextracted with ethyl acetate (2×30 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated
custompurified via flash chromatography
washeluting with 20% EtOAc and hexane

Sources & evidence

ORD record: ord-2fd47c259499410e83b2e32c31366bc1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056873B2

Reaction notes

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