Trifluoroacetic acid → HCID 25110308, compound

HRID 717734Notes

Reaction equation

HRID 717734 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[CH:21][NH:22]4)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].C1COCC1.C(O)(C(F)(F)F)=O>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][NH:22]4)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 251102975-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole

Product 1

HCID 25110308HCID 25110308, compoundYield 43%

Procedure

To a solution of the product of Step B (0.06 g; 0.172 mmol) in 1M BH3 in THF (0.35 ml; 0.35 mmol) TFA (0.4 ml) was added drop wise at 0° C. with stirring. After the addition was completed (˜5 min), the reaction was quenched with H2O (0.5 ml) and solvents were removed under reduced pressure. The residue was diluted to 10 ml with EtOAc and was washed with 10% NaOH (2×2 ml), brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound (0.026 g; 43%) as a creamy foam, which was used in the next step without further purification. 1H-NMR (CDCl3) 7.78 (dd, 1H, J=1.9, 7.2 Hz); 7.68 (d, 1H, J=1.9 Hz); 7.52 (d, 1H, J=7.2 Hz); 7.17 (t, 1H, J=7.7); 6.97 (d, 1H, J=8.5 Hz); 6.75 (d, 1H, J=7.7 Hz); 4.19 (m, 4H); 3.65 (t, 2H, J=8.9 Hz); 3.45 (tr, 2H, J=8.9 Hz); 1.7 (broad s, 1H+H2O); 1.49 (m, 6H).

Workup

  1. additionAfter the addition
  2. custom(˜5 min)
  3. customthe reaction was quenched with H2O (0.5 ml) and solvents
  4. customwere removed under reduced pressure
  5. additionThe residue was diluted to 10 ml with EtOAc
  6. washwas washed with 10% NaOH (2×2 ml), brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f3564f0095b740b4ac74f5a3cf016928
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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