Cesium fluoride → HCID 136200876, compound
Reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][N:9]=[N:8][CH:7]=1)CCC.I[C:21]1[CH:22]=[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[CH:24]=[CH:25][C:26]=1[OH:27].[F-].[Cs+]>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:9]1[CH:10]=[CH:11][C:6]([C:21]2[CH:22]=[C:23]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=3)[CH:24]=[CH:25][C:26]=2[OH:27])=[CH:7][N:8]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 4-(tributylstannyl)pyridazine (1.71 g, 4.64 mmol) and 3-iodo-3′-(trifluoromethyl)biphenyl-4-ol (Preparation 2, 1.30 g, 3.57 mmol) in N,N-dimethylformamide (20 mL) was added caesium fluoride (1.10 g, 7.14 mmol). The mixture was degassed before the addition of tetrakis(triphenylphosphine) palladium (0) (412 mg, 0.357 mmol), then heated to 45° C. for 4 hours. The reaction was concentrated in vacuo and purified by silica gel column chromatography (0%-20% methanol in dichloromethane gradient elution). The residue was triturated with acetonitrile and filtered to afford the title compound (420 mg, 37%) as a solid.
Workup
- concentrationThe reaction was concentrated in vacuo
- custompurified by silica gel column chromatography (0%-20% methanol in dichloromethane gradient elution)
- customThe residue was triturated with acetonitrile
- filtrationfiltered
Sources & evidence
- ORD record
- ord-4288ebe43fa44c86b00c89cd388d9808
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772293B2
Reaction notes
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