Trifluoroacetic acid → HCID 58203976, compound

HRID 1190750Notes

Reaction equation

HRID 1190750 reaction equation
[Cl-].C(OC([N:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[Zn+])=O)(C)(C)C.Br[C:16]1[CH:37]=[CH:36][C:19]2[C:20]3[N:21]=[C:22]([C:28]4[N:29]([CH:33]([CH3:35])[CH3:34])[N:30]=[CH:31][N:32]=4)[S:23][C:24]=3[CH2:25][CH2:26][O:27][C:18]=2[CH:17]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:33]([N:29]1[C:28]([C:22]2[S:23][C:24]3[CH2:25][CH2:26][O:27][C:18]4[CH:17]=[C:16]([CH:10]5[CH2:11][CH2:12][CH2:13][NH:9]5)[CH:37]=[CH:36][C:19]=4[C:20]=3[N:21]=2)=[N:32][CH:31]=[N:30]1)([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 668867488-Bromo-2-isopropyl-2H-1,2,4-triazol-3-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azuleneHCID 178451953HCID 178451953, compound

Product 1

HCID 58203976HCID 58203976, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

(1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)zinc(II) chloride (2.75 mL, 1.02 mmol, 0.37M) was added to a 10 mL microwave vial under nitrogen, 8-Bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene 27 from FIG. 4 (200 mg, 0.51 mmol), Pd(OAc)2 (12 mg) and tri-tert-butylphosphonium tetrafluoroborate (18 mg) were added. The reaction vessel was sealed and the mixture heated at 100° C. overnight. Aqueous work-up and concentration gave a crude residue which was treated with TFA in DCM (1:1 mix). After 1 h at room temperature, the solvent was removed and the residue purified by reverse phase HPLC to give 537 (10 mg, 5%). LCMS: 382.1

Workup

  1. additionwere added
  2. customThe reaction vessel was sealed
  3. concentrationAqueous work-up and concentration
  4. customgave a crude residue which
  5. customthe solvent was removed
  6. customthe residue purified by reverse phase HPLC

Sources & evidence

ORD record
ord-aaa876991695430da6292f64d03df13f
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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