Water → HCID 49832489, compound

HRID 1947521Notes

Reaction equation

HRID 1947521 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=O)=[CH:14]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[N:22]1([CH2:20][C:15]2[NH:16][C:17]3[C:13]([CH:14]=2)=[CH:12][C:11]([O:10][C:2]2[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=2)=[CH:19][CH:18]=3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59577496HCID 59577496, compound

Product 1

HCID 49832489HCID 49832489, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of [5-(benzothiazol-2-yloxy)-1H-indol-2-yl]-piperidin-1-yl-methanone (150 mg, 0.40 mmol) in THF (5 mL) was added LAH (2 M in THF, 0.2 mL, 18 mg, 0.40 mmol) and the reaction mixture was stirred (−78° C., 1 h) and allowed to warm (rt, 1 h). The reaction mixture was cooled (0° C.) and treated with H2O (5 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3×15 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH:DCM (0-8%) to provide the title compound as a colorless foam (78 mg, 54%). MS (ESI): mass calcd. for O21H21N3OS, 363.1; m/z found, 364.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.64 (s, 1H), 7.77-7.70 (m, 1H), 7.61 (dd, J=7.9, 0.7, 1H), 7.48 (d, J=2.3, 1H), 7.40-7.32 (m, 2H), 7.22 (dd, J=11.0, 4.3, 1H), 7.10 (dd, J=8.7, 2.4, 1H), 6.35 (s, 1H), 3.62 (s, 2H), 2.60-2.30 (m, 4H), 1.65-1.54 (m, 4H), 1.53-1.41 (m, 2H).

Workup

  1. temperatureto warm (rt, 1 h)
  2. temperatureThe reaction mixture was cooled (0° C.)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×15 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-6392b15c8de743f0b1f52615b5301902
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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