Ethyl Acetate → HCID 58994480, compound

HRID 1508153Notes

Reaction equation

HRID 1508153 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:4][C:3]=1[NH2:20].[CH3:21][C:22]1([CH3:31])[CH2:27][CH2:26][C:25](B(O)O)=[CH:24][CH2:23]1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.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:14]([Si:11]([CH3:13])([CH3:12])[O:10][CH2:9][C:8]([C:6]1[CH:5]=[CH:4][C:3]([NH2:20])=[C:2]([C:25]2[CH2:26][CH2:27][C:22]([CH3:31])([CH3:21])[CH2:23][CH:24]=2)[CH:7]=1)([CH3:19])[CH3:18])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 441195554,4-Dimethylcyclohexen-1-ylboronic acidHCID 58994555HCID 58994555, compound

Product 1

HCID 58994480HCID 58994480, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 2-bromo-4-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-phenylamine (as prepared in the previous step, 1.50 g, 4.19 mmol), 4,4-dimethylcyclohexen-1-ylboronic acid (1.09 g, 4.61 mmol) and Pd(PPh3)4 (484 mg, 0.419 mmol) in 50 mL of 1,4-dioxane was added aqueous Na2CO3 (16.8 mL, 33.5 mmol, 2.0 M). The resulting mixture was stirred at 90° C. for 16 h under Ar. After cooling to RT, the mixture was treated with 150 mL of EtOAc and washed with H2O (3×30 mL) and brine (30 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (5-10% EtOAc/hexane) to afford 1.46 g (90%) of the title compound as a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C24H41NOSi, 388.3 (M+H). found 388.3.

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with H2O (3×30 mL) and brine (30 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (5-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-3ee2525283bd4a79964bc15e2f16ed00
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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