Pentane → 1-(tert-Butyl-dimethyl-silanyl)-5-tributylstannanyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C:5]2=[N:6][CH:7]=1.C([Li])(C)(C)C.CCCCC.[CH2:28]([Sn:32](I)([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH3:31]>C1COCC1>[C:14]([Si:11]([CH3:13])([CH3:12])[N:8]1[C:5]2=[N:6][CH:7]=[C:2]([Sn:32]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:28][CH2:29][CH2:30][CH3:31])[CH:3]=[C:4]2[CH2:10][CH2:9]1)([CH3:17])([CH3:16])[CH3:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred and cooled (−90° C.) solution of bromide 4 (206 mg, 0.66 mmol) in THF (2.5 mL) was added dropwise 1.5 M solution of tert-butyllithium in pentane (1 mL, 1.51 mmol). After 35 min additional stirring at −90° C., tri-n-butyltin iodide (0.23 mL, 0.79 mmol) was added in one portion. The mixture was stirred at −90° C. for 10 min, −78° C. for 40 min, and then allowed to warm to r.t. The mixture was partitioned between AcOEt-brine. The aqueous layer was extracted with AcOEt (3×) and the combined organic solutions were dried (MgSO4), and concentrated to afford the crude stannane 17, which was used in the next step without purification.
Workup
- stirringAfter 35 min additional stirring at −90° C.
- stirringThe mixture was stirred at −90° C. for 10 min, −78° C. for 40 min
- customThe mixture was partitioned between AcOEt-brine
- extractionThe aqueous layer was extracted with AcOEt (3×)
- dry with materialthe combined organic solutions were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-55b6451863be4857bc7c0456a5e3a44e
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652137B2
Reaction notes
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