Potassium Fluoride → 4-(4-Chloro-6-thiophen-3-yl-[1,3,5]triazin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[C:18](Cl)[N:17]=[C:16]([Cl:21])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1.[F-].[K+]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:15]=[C:16]([Cl:21])[N:17]=[C:18]([C:24]3[CH:25]=[CH:26][S:22][CH:23]=3)[N:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 4-(4,6-dichloro-[1,3,5]triazin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (167.1 mg, 0.5 mmol) in anhydrous 1,4-dioxane (4 mL) in an oven-dried flask was added 3-thiopheneboronic acid (70.4 mg, 0.55 mmol), Pd[P(t-Bu)3]2 (2.5 mg, 0.005 mmol), tris(dibenzylideneacetone)-dipalladium(0) (2.3 mg, 0.0025 mmol), and KF (64 mg, 1.1 mmol). The resulting mixture was vacuum flushed with argon and heated overnight at 90° C. The reaction mixture was cooled and passed through a pad of diatomaceous earth, washing with EtOAc. The filtrate was concentrated and the residue was purified by preparative TLC (EtOAc/hexanes, 1:4) to yield a white solid, which was used without further purification.
Workup
- customflushed with argon
- temperatureThe reaction mixture was cooled
- washwashing with EtOAc
- concentrationThe filtrate was concentrated
- customthe residue was purified by preparative TLC (EtOAc/hexanes, 1:4)
- customto yield a white solid, which
- customwas used without further purification
Sources & evidence
- ORD record
- ord-6739acb440234ef59eba849505fe86db
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022209B2
Reaction notes
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