Triethylamine → HCID 12085088, compound

HRID 1358120Notes

Reaction equation

HRID 1358120 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]3[C:19]([O:20][CH:21]([F:23])[F:22])=[CH:18][CH:17]=[CH:16][C:7]=3[O:8][CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[C:3]=1Br.C(N(CC)CC)C.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]3[C:19]([O:20][CH:21]([F:23])[F:22])=[CH:18][CH:17]=[CH:16][C:7]=3[O:8][CH:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10112712HCID 10112712, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12085088HCID 12085088, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 4 (1.19 g), triethylamine (2.8 mL) and 10% Pd/C (120 mg) in ethyl acetate (100 mL) was shaken under 1.5 atms. hydrogen for 15 minutes. The mixture was filtered and concentrated under reduced pressure. The residue was taken up in toluene (50 mL), washed with aqueous KHCO3, dried (Na2SO4), filtered and concentrated. The resulting material was purified on silica eluting with 25% hexane −75% CH2Cl2 to provide the titled compound (0.763 g, 80%). 1H NMR (300 MHz, CDCl3) δ 3.75 (br s, 2H), 5.95 (s, 1H), 6.14 (d, J=3 Hz, 1H), 6.50 (t, J=75 Hz, 1H, CHF2) 6.71 (dd, J=9 Hz, 3 Hz, 1H), 6.77 (dd, J=9 Hz, 1Hz, 1H), 6.87 (dd, J=9 Hz, 1Hz, 1H), 7.05 (t, J=8 Hz, H), 7.30-7.40 (m, 5H), 8.12 (d, J=9 Hz, 1H). MS (APCI) m/e 340 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. washwashed with aqueous KHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting material was purified on silica eluting with 25% hexane −75% CH2Cl2

Sources & evidence

ORD record
ord-d2bd541fc5174afcadd17a0cadcf2c05
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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