Triisopropyl borate → HCID 89500809, compound
Reaction equation
[Cl:1][C:2]1[S:9][C:8]2[CH:7]=[CH:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4]=2[CH:3]=1.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[C:13]([O:12][C:10]([N:5]1[C:6]([B:17]([OH:22])[OH:18])=[CH:7][C:8]2[S:9][C:2]([Cl:1])=[CH:3][C:4]1=2)=[O:11])([CH3:16])([CH3:15])[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 2-chloro-4H-thieno[3,2-b]pyrrole-4-carboxylate (0.52 g, 2 mmol) and B(OiPr)3 (0.7 mL, 3 mmol) in 10 mL of THF cooled at 0° C. was added a LDA solution (4 mmol, prepared from 0.56 mL of iPr2NH, 5.84 mL of THF and 1.6 mL of 2.5 M n-BuLi solution in hexane) by a syringe pump over a period of 2 h. The reaction mixture was stirred for additional 6 h at 0° C. before being quenched by addition of 20 mL of saturated NH4Cl solution. The product was extracted with 2×20 mL of EtOAc, dried over Na2SO4, filtered and concentrated. The residue was purified by Combiflash on a silica gel column eluted with a gradient of up to 60% EtOAc/hexanes to give 0.3 g of the title compound as a solid.
Workup
- custombefore being quenched by addition of 20 mL of saturated NH4Cl solution
- extractionThe product was extracted with 2×20 mL of EtOAc
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by Combiflash on a silica gel column
- washeluted with a gradient of up to 60% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-84ef836097a7462aade2bd4fca5d9074
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946445B2
Reaction notes
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