Cesium carbonate → HCID 67413047, compound
Reaction equation
[F:1][C:2]1([F:27])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:14][C:9]=2[N:8]([CH3:24])[S:7]1(=[O:26])=[O:25].Br[C:29]1[N:34]=[C:33]([CH2:35][OH:36])[CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.CCOC(C)=O.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[F:27][C:2]1([F:1])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:29]3[N:34]=[C:33]([CH2:35][OH:36])[CH:32]=[CH:31][CH:30]=3)=[CH:14][C:9]=2[N:8]([CH3:24])[S:7]1(=[O:25])=[O:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 120 °C
Procedure
1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (12-1) (131 mg, 0.33 mmol, 1.0 eq), (6-bromopyridin-2-yl)methanol (61 mg, 0.33 mmol, 1.0 eq), cesium carbonate (317 mg, 0.97 mmol, 3.0 eq) and bis(tri-t-butylphosphine) palladium(0) (16.6 mg, 0.03 mmol, 0.1 eq) were combined in dioxane (1.0 mL) and water (0.2 mL). The resulting mixture was heated in the microwave at 120° C. for 20 minutes. The reaction mixture was diluted with EtOAc (10 mL), washed with water (2 mL) and brine (2 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (12 g SiO2, 0-80% EtOAc in hexanes) to afford (6-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}pyridin-2-yl)methanol (25-1). LRMS m/z (M+H) 382.2 found, 382.1 required.
Workup
- washwashed with water (2 mL) and brine (2 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was purified by flash chromatography (12 g SiO2, 0-80% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-561e41129dc546d481f8a1769dff119e
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108937B2
Reaction notes
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