Ethyl Acetate → HCID 59275318, compound

HRID 1877600Notes

Reaction equation

HRID 1877600 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-])=O)[C:18]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:41])[NH:31][C:32]5([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[CH2:34][CH2:33]5)[CH:25]=4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.C(OCC)(=O)C>CN(C=O)C.[Pd]>[NH2:21][C:19]1[C:18]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:41])[NH:31][C:32]3([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:33][CH2:34]3)[CH:25]=2)=[CH:17][C:11]2[C:12]([C:13]([NH:15][CH3:16])=[O:14])=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:9][C:10]=2[CH:20]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59275160HCID 59275160, compound

Product 1

HCID 59275318HCID 59275318, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(4-Fluorophenyl)-N-methyl-6-nitro-5-(3-(1-phenylcyclopropylcarbamoyl)phenyl)benzofuran-3-carboxamide (83.3 mg, 0.152 mmol) undr N2 at r.t. was dissolved in DMF (2 ml) and then added ethyl acetate (10 mL). The mixture remained as a clear light brown solution. The mixture was added palladium (97 mg, 0.045 mmol, 5%/C), flushed with H2 using a balloon, and the mixture stirred under H2 for about 8 hr. The mixture was diluted with EtOAc, and filtered through a Whatman PTFE 45 uM disk. The filtrate was evaporated. The residue was titurated with 3×1 ml Et2O (the Et2O solution was removed by using a pipette), and the light orange solid product dried (64.4 mg, 82%). 1H NMR (500 MHz, DMSO-d6) δ 9.26 (s, 1H), 8.32 (q, J=4.17, 1H), 7.94-7.89 (overlapping m, 3H), 7.97 (s, 1H), 7.62 (d, J=6.8, 1H), 7.58 (q, 1H), 7.34 (t, J=8.70, 2H), 7.29 (t, 1H), 7.28 (d, J=7.50, 1H), 7.23 (s, 2H), 7.227 (d, J=8.00, 1H), 7.17 (t, J=7.17, 1H,), 6.99 (s, 1H), 5.09 (s, 2H), 2.79 (appeared as d, J=3.97, 3H), 1.29 (appeared as d, 4H). LC/MS were performed by using Shimadzu-VP instrument with UV detection at 220 nm and Waters Micromass. HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Stop time=3 min, Flow Rate=4 ml/min, Column: Xterra MS 7 um, C18, 3.0×50 mm; (ES+) m/z (M+H)+=520.39, HPLC Rt=1.497 min.

Workup

  1. customflushed with H2 using a balloon
  2. additionThe mixture was diluted with EtOAc
  3. filtrationfiltered through a Whatman PTFE 45 uM disk
  4. customThe filtrate was evaporated
  5. customwas removed
  6. customdried (64.4 mg, 82%)
  7. customB=100, Gradient time=2 min
  8. customtime=3 min, Flow Rate=4 ml/min, Column

Sources & evidence

ORD record
ord-604853868b9147bd85b49ea19e465ba2
Source dataset
uspto-grants-2012_11
Patent number
US08309558B2

Reaction notes

Loading…