Water → HCID 49869933, compound
Reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:4]=1[S:18]([NH:21][C@H:22]1[CH2:27][CH2:26][CH2:25][C@@H:24]([N:28]2[CH:32]=[N:31][N:30]=[CH:29]2)[CH2:23]1)(=[O:20])=[O:19])[CH3:2].Br[C:34]1[C:35]2[N:36]([CH:40]=[CH:41][N:42]=2)[CH:37]=[CH:38][CH:39]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.CCOC(C)=O.CCO>[CH2:1]([C:3]1[CH:8]=[C:7]([C:34]2[C:35]3[N:36]([CH:40]=[CH:41][N:42]=3)[CH:37]=[CH:38][CH:39]=2)[CH:6]=[CH:5][C:4]=1[S:18]([NH:21][C@H:22]1[CH2:27][CH2:26][CH2:25][C@@H:24]([N:28]2[CH:29]=[N:30][N:31]=[CH:32]2)[CH2:23]1)(=[O:19])=[O:20])[CH3:2]Participants
Conditions
- Temperature
- 120 °C
Procedure
Compound 2c (1.50 mL of a 0.1 M DME solution, 0.150 mmol) was added to a mixture of 8-bromoimidazo[1,2-a]pyridine (29.6 mg, 0.150 mmol), sodium carbonate (150 μL of a 2 M aq. solution, 0.300 mmol) and tetrakistriphenylphosphine palladium(0) (17.3 mg, 0.015 mmol) in DME:water:EtOH (2.00 mL of a 12:4:3 mixture, respectively). The reaction mixture was placed in a sealed tube and heated in a microwave reactor at 120° C. for 15 min. After cooling to rt, the mixture was diluted with EtOAc and filtered through a short column Celite®, eluting copiously with EtOAc. The combined organics were concentrated in vacuo, and the resulting crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent) to afford the title compound, 2d. m/z (ES) 453 (MH)+. IC50=3.9 nM
Workup
- customThe reaction mixture was placed in a sealed tube
- temperatureAfter cooling to rt
- filtrationfiltered through a short column Celite®
- washeluting copiously with EtOAc
- concentrationThe combined organics were concentrated in vacuo
- customthe resulting crude residue was purified by preparative thin layer chromatography on silica gel (10% MeOH/DCM as eluent)
Sources & evidence
- ORD record
- ord-946d72d4078d416bb302baf34da8c85c
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029377B2
Reaction notes
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