Triethylamine → HCID 66869797, compound

HRID 1422645Notes

Reaction equation

HRID 1422645 reaction equation
[OH:1][C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:14][C:15]([CH3:17])=[CH2:16])[CH2:3][CH2:4][N:5]([C:9]([CH3:13])([C:11]#[CH:12])[CH3:10])[C:6](=[O:8])[O-:7].Br[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.[CH3:32]CN(CC)CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:12]#[C:11][C:9]([N:5]([CH2:4][CH2:3][C:2]([OH:1])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:14][C:15]([CH3:17])=[CH2:16])[C:6](=[O:7])[O:8][CH3:32])([CH3:10])[CH3:13])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99931-Bromo-4-fluorobenzeneHCID 86669138HCID 86669138, compound

Product 1

HCID 66869797HCID 66869797, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A microwave vial equipped with a flea stir bar was charged with 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-methylbut-3-yn-2-yl)carbamate (37 mg, 0.11 mmol), 1-bromo-4-fluorobenzene (39 mg, 0.22 mmol), Cul (2 mg, 0.011 mmol), Pd(PPh3)2Cl2 (4.7 mg, 0.007 mmol) and Et3N (1.5 mL). The mixture was sparged with N2 for 5 min and heated at 100 C for 2 h in the microwave. The mixture was concentrated and the residue was redissolved in EtOAc (90 mL), washed with 5% aq HCl (15 mL), satd aq NaHCO3 (15 mL) and brine (15 mL), and dried over Na2SO4. Removal of the solvent left an orange oil (46 mg) which was applied to a 2-g silica SPE cartridge and eluted sequentially with 0, 10, 25, 50 and 100% EtOAc in hexanes (15 mL of each) to give five fractions. Fractions 2 and 3 were pooled and concentrated to afford methyl 4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl(3-hydroxy-5-methyl-3-phenylhex-5-enyl)carbamate (35 mg, 73%) as an oil. LC-MS Method 1 tR=2.33 min, 406 (M−18).

Workup

  1. customA microwave vial equipped with a flea
  2. customThe mixture was sparged with N2 for 5 min
  3. temperatureheated at 100 C for 2 h in the microwave
  4. concentrationThe mixture was concentrated
  5. dissolutionthe residue was redissolved in EtOAc (90 mL)
  6. washwashed with 5% aq HCl (15 mL)
  7. dry with materialdried over Na2SO4
  8. customRemoval of the solvent
  9. waitleft an orange oil (46 mg) which
  10. washeluted sequentially with 0, 10, 25, 50 and 100% EtOAc in hexanes (15 mL of each)
  11. customto give five fractions
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-23813ca95a8c426b80a6a3748d09cfc4
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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