Sodium Carbonate → HCID 83390807, compound
Reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:23]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH:12]=[C:11]([C:23]2[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]=2)[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
To 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (406 mg, 1.43 mmol), 3-bromocyclohex-2-enone (200 mg, 1.14 mmol), and Pd(PPh3)4 (132 mg, 0.114 mmol) in toluene (2 mL) was added 2M Na2CO3 (1 mL). The reaction mixture was purged with nitrogen and heated at 110° C. for 16 h. The reaction was diluted with water (10 mL) and extracted DCM (3×15 mL), dried over Na2SO4 and purified by flash chromatography (24 g silica gel) using hexanes/EtOAc (0-50% over 15 min, flow rate 35 mL/min) to isolate Intermediate 45A (160 mg, 0.634 mmol, 55.5% yield) as a tan solid. LC-MS (ESI) 253.0 (M+H), RT=1.70 min (Method B).
Workup
- customThe reaction mixture was purged with nitrogen
- additionThe reaction was diluted with water (10 mL)
- extractionextracted DCM (3×15 mL)
- dry with materialdried over Na2SO4
- custompurified by flash chromatography (24 g silica gel)
- customhexanes/EtOAc (0-50% over 15 min, flow rate 35 mL/min)
Sources & evidence
- ORD record
- ord-bc42101a048d4b8381bf5f02ca21dfd0
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199946B2
Reaction notes
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