Potassium Carbonate → HCID 86282349, compound

HRID 2275424Notes

Reaction equation

HRID 2275424 reaction equation
[CH3:1][C:2]([CH3:19])([C@H:4]([N:7]([C:9](=[O:18])[C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[CH:11]=1)[NH2:8])[CH2:5][CH3:6])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[F:26][C:27]1[CH:35]=[C:34]([B:36]2[O:40]C(C)(C)C(C)(C)[O:37]2)[CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>C(Cl)Cl.O>[CH3:17][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([CH3:16])[CH:13]=1)[C:9]([N:7]([C@H:4]([CH2:5][CH3:6])[C:2]([CH3:1])([CH3:3])[CH3:19])[NH:8][C:29]([C:28]1[CH:32]=[CH:33][C:34]([B:36]([OH:40])[OH:37])=[CH:35][C:27]=1[F:26])=[O:30])=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 90408395HCID 90408395, compoundHCID 90409492HCID 90409492, compound

Product 1

HCID 86282349HCID 86282349, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

In a 25 mL round bottom flask equipped with a magnetic stir bar were added (R)—N-(2,2-dimethylpentan-3-yl)-3,5-dimethylbenzohydrazide (1.317 g, 5.02 mmol) in 7 mL CH2Cl2 and a solution of potassium carbonate (1.388 g, 10.04 mmol) in distilled water (4 mL) were cooled in an ice bath at 0-4° C. and stirred for 10 min. The 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride (1.714 g, 6.02 mmol) was added as a solution in 3.5 mL dichloromethane. The reaction was stirred at 0-4° C. for 30 min., the ice bath was removed and the mixture was stirred for 16 h at room temperature. The reaction was analyzed by LCMS and shows the reaction was complete. The organic layer was separated using a Biotage phase separator column and was transferred to a 40 g Redisep SiO2 column on the ISCO HPLC system. The compound was eluted with 0-100% EtOAc—hexanes and then with 10% MeOH—CH2Cl2. The desired fractions were combined and concentrated on a rotary evaporator to give the desired compound as an off-white foam (1.518 g, 59% yield). MS (ESI) calcd for C29H40BFN2O4 ([M+H]+) 511. found 511.

Workup

  1. customIn a 25 mL round bottom flask equipped with a magnetic stir bar
  2. stirringThe reaction was stirred at 0-4° C. for 30 min.
  3. customthe ice bath was removed
  4. stirringthe mixture was stirred for 16 h at room temperature
  5. customThe organic layer was separated
  6. washThe compound was eluted with 0-100% EtOAc—hexanes
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-dbc722a43e6245d187c655f4fc4214b6
Source dataset
uspto-grants-2015_09
Patent number
US09127024B2

Reaction notes

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