Triethylamine → HCID 58444590, compound

HRID 1509766Notes

Reaction equation

HRID 1509766 reaction equation
Br[CH:2]1[CH:7]([CH2:8][CH3:9])[CH2:6][O:5][CH:4]([C:10]2[CH:15]=[CH:14][C:13]([B:16]3[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]3)=[C:12]([F:25])[CH:11]=2)[CH2:3]1.[H][H].C(N(CC)CC)C>C1(C)C=CC=CC=1.O.[Pd]>[CH2:8]([CH:7]1[CH2:6][O:5][CH:4]([C:10]2[CH:15]=[CH:14][C:13]([B:16]3[O:17][C:18]([CH3:24])([CH3:23])[C:19]([CH3:22])([CH3:21])[O:20]3)=[C:12]([F:25])[CH:11]=2)[CH2:3][CH2:2]1)[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 58444576HCID 58444576, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58444590HCID 58444590, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22272177Toluene waterSolvent

Procedure

18.0 g (36.2 mmol) of 4-bromo-5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran are hydrogenated for 30 h at a hydrogen pressure of 5 bar and at 80° C. in toluene/water in the presence of Pd/C (5% of Pd) and 12.7 ml (88.1 mmol) of triethylamine. The organic phase is separated off and filtered absorptively (SiO2, toluene). The filtrate is concentrated to dryness, and the residue is recrystallised from ethanol at reduced temperature, giving 5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran as a colourless solid.

Workup

  1. customThe organic phase is separated off
  2. filtrationfiltered absorptively (SiO2, toluene)
  3. concentrationThe filtrate is concentrated to dryness
  4. customthe residue is recrystallised from ethanol at reduced temperature

Sources & evidence

ORD record
ord-2b094232b48642f2a451f1a7b0685be9
Source dataset
uspto-grants-2012_07
Patent number
US08211513B2

Reaction notes

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