Water → HCID 67148403, compound

HRID 2428149Notes

Reaction equation

HRID 2428149 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:11][C:12]1[CH:17]=[C:16](Br)[CH:15]=[CH:14][C:13]=1[Cl:19])[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].O.[CH3:28][C:29]1(C)C(C)(C)OB(C=C)O1>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:11][C:12]1[CH:17]=[C:16]([CH:28]=[CH2:29])[CH:15]=[CH:14][C:13]=1[Cl:19])[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66762093HCID 66762093, compound

Product 1

HCID 67148403HCID 67148403, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a sol. of (5-bromo-2-chloro-benzyl)-cyclopropyl-carbamic acid tert-butyl ester (105 g, 0.292 mol) in DME (800 mL) under N2 at rt was added Pd(PPh3)4 (16.9 g, 14.6 mmol). The mixture was stirred at rt for 30 min, and K2CO3 (40.7 g, 292 mmol), water (350 mL) and 4,4,5,5-tetramethyl-2-vinyl-[1,3,2]dioxaborolane (52.0 mL, 292 mmol) were added. The mixture was heated to reflux for 3 h. The mixture was allowed to cool to rt, and water (500 mL) was added. The mixture was extracted with Et2O (4×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (heptane/EtOAc 9:1) yielded the title compound (70.9 g, 79%). LC-MS: tR=1.10 min; ES+: 293.38.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. temperatureto cool to rt
  4. extractionThe mixture was extracted with Et2O (4×)
  5. dry with materialextracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the crude by FC (heptane/EtOAc 9:1)

Sources & evidence

ORD record
ord-b2c329182577434b88a9fc29286155c5
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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