Triethylamine → HCID 59272319, compound

HRID 1970284Notes

Reaction equation

HRID 1970284 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16][CH3:17])=[CH:9][CH:10]=3)[C@@:5]3([CH2:21][O:20][C:19]([NH2:22])=[N:18]3)[C:4]=2[CH:3]=1.[CH2:23]([N:25]([CH2:28][CH3:29])[CH2:26]C)[CH3:24].N1CCCC1.[O:35]1CCOCC1>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].CCOC(C)=O.C([O-])(O)=O.[Na+]>[NH2:22][C:19]1[O:20][CH2:21][C@:5]2([N:18]=1)[C:6]1[CH:7]=[C:8]([O:16][CH3:17])[CH:9]=[CH:10][C:11]=1[O:12][C:13]1[C:4]2=[CH:3][C:2]([C:26]([N:25]2[CH2:28][CH2:29][CH2:24][CH2:23]2)=[O:35])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 312751,4-DioxaneHCID 67242444HCID 67242444, compound

Product 1

HCID 59272319HCID 59272319, compound

Reagents, catalysts & solvents 3

HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)CatalystHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A microwave vial charged with (S)-2′-bromo-7′-methoxy-5H-spiro[oxazole-4,9′-xanthen]-2-amine (100 mg, 277 μmol), Mo(CO)6 (Strem, 37 mg, 138 μmol), Herrmann's catalyst (Strem, 13 mg, 14 μmol), triethylamine (39 μL, 277 μmol), pyrrolidine (Fluka, 23 μL, 277 μmol), and 1,4-dioxane (0.5 mL, 5.8 mmol) was sealed and irradiated to 170° C. for 10 min. The mixture was diluted with EtOAc and saturated NaHCO3, extracted 3× with EtOAc. The organic layers were combined and dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by reverse phase prep HPLC: 35-100% CH3CN (0.1% TFA)-water (0.1% TFA) in 15 min. The fractions were combined and neutralized with solid Na2CO3, extracted 3×CH2Cl2. The organic layer was dried over Na2SO4 and concentrated in vacuo. The product was obtained as a white solid. MS m/z=380 [M+H]+.

Workup

  1. customwas sealed
  2. customirradiated to 170° C. for 10 min
  3. extractionextracted 3× with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by reverse phase prep HPLC
  7. extractionextracted 3×CH2Cl2
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-52845a18606648e5afdf8f3112888389
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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