N-bromobutanimide → HCID 90408806, compound
Reaction equation
[F:1][C:2]1[C:11]([B:12]2[O:16]C(C)(C)C(C)(C)[O:13]2)=[C:10]([CH3:21])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].BrN1C(=O)CCC1=O.N(/C1(C#N)CCCCC1)=N\C1(C#N)CCCCC1>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[C:11]2[B:12]([OH:13])[O:16][CH2:21][C:10]=2[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution or methyl 2-fluoro-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.6 g, 2.040 mmol) in 40 ml CCl4 was added N-Bromosuccinimide (0.363 g, 2.040 mmol) and (E)-1,1′-(diazene-1,2-diyl)dicyclohexanecarbonitrile (0.050 g, 0.204 mmol). The mixture was stirred at 80° C. overnight. The reaction mixture was extracted with 5% KOH in water (3×20 ml). The water phase stirred for 1 hour and then the solution was cooled to 0° C. and slowly acidified to pH<1 with 1N HCl. The precipitant that formed was filtered onto fritted filter and dried in vacuum for overnight to give 0.137 g of IXS-5-49-1, 1H NMR in DMSO-d6 is consistent with desired product. MS [MH+]=196.
Workup
- extractionThe reaction mixture was extracted with 5% KOH in water (3×20 ml)
- stirringThe water phase stirred for 1 hour
- temperaturethe solution was cooled to 0° C.
- customThe precipitant that formed
- filtrationwas filtered onto fritted filter
- customdried in vacuum for overnight
- customto give 0.137 g of IXS-5-49-1, 1H NMR in DMSO-d6
Sources & evidence
- ORD record
- ord-fed237331ea4422294d33c24bcc3971b
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09127024B2
Reaction notes
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