Tributyltin Chloride → 7-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[Li]CCCC.[CH2:16]([Sn:20]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])Cl)[CH2:17][CH2:18][CH3:19].CCOC(C)=O.CCCCCC>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Sn:20]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:16][CH2:17][CH2:18][CH3:19])[S:10][C:3]=12Participants
6
Procedure
To a solution of the chloride 2 (18.72 g, 110 mmol) in THF (200 mL) at −78° C. n-BuLi (51 mL, 127 mmol) was added and the reaction mixture was stirred for about 30 minutes. The tributylchlorostannane (25.4 mL, 93 mmol) was added and the mixture was stirred at −78° C. for another 60 minutes, quenched with water [at the same temperature] and allowed to warm up to room temperature. The warmed mixture was extracted with EtOAc, the extract was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography, eluents EtOAc-hexane (15:85), then EtOAc-hexane (25:75) to afford title compound 98 (30.2 g, 77% yield) as a yellow oil. LRMS (M+1) 459.1 (100%).
Workup
- stirringthe mixture was stirred at −78° C. for another 60 minutes
- customquenched with water [at the same temperature] and
- extractionThe warmed mixture was extracted with EtOAc
- dry with materialthe extract was dried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified by flash chromatography, eluents EtOAc-hexane (15:85)
Sources & evidence
- ORD record
- ord-ab5e75d29db14f81838198b02fc2c7e7
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470850B2
Reaction notes
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