Tetrahydrofuran → HCID 131734940, compound

HRID 921850Notes

Reaction equation

HRID 921850 reaction equation
[Cl:1][C:2]1[C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]([C:17]#[N:18])=[CH:4][C:3]=1[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:36](=[CH2:40])[CH2:37][CH2:38][OH:39].C1COCC1>CCOC(C)=O.CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+].O>[Cl:1][C:2]1[C:7]([C:36]([CH2:37][CH2:38][OH:39])=[CH2:40])=[CH:6][C:5]([C:17]#[N:18])=[CH:4][C:3]=1[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 5339753-Bromo-3-buten-1-olHCID 131734937HCID 131734937, compound

Product 1

HCID 131734940HCID 131734940, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 54751079XPhos PalladacycleCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Tert-butyl (2-chloro-5-cyano-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (864 mg, 2.282 mmol), (2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) chloride (84 mg, 0.114 mmol), and potassium phosphate, dibasic (1192 mg, 6.85 mmol) were added to a 100 ml flask, and the flask was purged with N2. 3-bromobut-3-en-1-ol (0.226 mL, 2.282 mmol) and THF (12 mL) were added, followed by water (2.182 mL). The reaction was heated at 60° C. for 1 h. The reaction was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water, then brine, dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0-50% EtOAc/Hex; 120 g column). Tert-butyl (2-chloro-5-cyano-3-(4-hydroxybut-1-en-2-yl)phenyl)carbamate (317 mg) was obtained as a colorless glass.

Workup

  1. customthe flask was purged with N2
  2. temperatureThe reaction was cooled to room temperature
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash column chromatography (0-50% EtOAc/Hex; 120 g column)

Sources & evidence

ORD record
ord-10348b32897c49b6ac8e9262ba89bed1
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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