Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate → HCID 10272130, compound

HRID 432085

Reaction equation

HRID 432085 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)O1.I[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[O:27][C@@H:26]([CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:25][CH2:24]2>C1(C)C=CC=CC=1.O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:35]([O:34][C:33]([NH:32][CH2:31][C@H:26]1[CH2:25][CH2:24][C:23]2[C:28](=[CH:29][CH:30]=[C:21]([C:9]3[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=3)[CH:22]=2)[O:27]1)=[O:39])([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 2

HCID 2773500Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 10221906HCID 10221906, compound

Product 1

HCID 10272130HCID 10272130, compoundYield 83.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Example 15, 1.67 g, 6.36 mmol) in 130 mL toluene and 27 mL 1,4-dioxane was degassed with argon for 10 minutes. tert-Butyl [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methylcarbamate (Example 12, 1.65 g) and 265 mg (3 mol %) Pd(dppf)Cl2 were then added, and the solution was degassed with argon for an additional 5 minutes. Finally, 26.5 mL of 2M aqueous sodium carbonate was added and the solution was stirred at 85° C. for 16 hours. This mixture was then cooled to ambient temperature, filtered through a pad of Celite®, and concentrated in vacuo. The product was then purified by Biotage (100% methylene chloride to 3% MeOH: methylene chloride) to obtain 1.40 g of product. m/z=397.9 [M+].

Workup

  1. customthe solution was degassed with argon for an additional 5 minutes
  2. additionFinally, 26.5 mL of 2M aqueous sodium carbonate was added
  3. temperatureThis mixture was then cooled to ambient temperature
  4. filtrationfiltered through a pad of Celite®
  5. concentrationconcentrated in vacuo
  6. customThe product was then purified by Biotage (100% methylene chloride to 3% MeOH: methylene chloride)

Sources & evidence

ORD record
ord-9d8838465fa346c18a12405a453ab4d5
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Linked notes

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