Aluminium lithium hydride → HCID 68817902, compound

HRID 735208Notes

Reaction equation

HRID 735208 reaction equation
C(O[C:4]([N:6]1[CH2:28][CH2:27][C:9]2[N:10]([CH3:26])[C:11]3[C:12]([S:17][C:18]4[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=4)=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:4][N:6]1[CH2:28][CH2:27][C:9]2[N:10]([CH3:26])[C:11]3[C:12]([S:17][C:18]4[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=4)=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[CH2:7]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68816188HCID 68816188, compound

Product 1

HCID 68817902HCID 68817902, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a dry THF solution (2 mL) of ethyl-5-methyl-6-{[4-(methylsulfanyl)phenyl] sulfanyl}-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (0.17 g, 0.41 mmol) was added dropwise over 15 min a THF solution of lithium aluminum hydride (1 mL, 1M in THF) at 0° C. The reaction was stirred at room temperature for 1 h. The reaction was quenched with water (0.04 mL) and stirred for 110 minutes. A 15% sodium hydroxide solution (0.04 mL) was added and stirred for 10 minutes, and water (0.12 mL) was added and stirred for 10 minutes. The resultant solids were filtered and washed with chloroform (10 mL). The filtrate was concentrated under reduced pressure. The resulted residue was purified by silica gel column chromatography, (3% methanol/chloroform) to afford 2,5-dimethyl-6-{[4-(methylsulfanyl)phenyl] sulfanyl}-2,3,4,5-tetrahydro-1H-pyrido [4,3-b]indole (78 mg, 54%) as a pale-yellow colored oil. 1H NMR (CDCl3, 300 MHz) δ 7.30 (d, 1H, J=7.3 Hz), 7.09-7.02 (m, 3H), 6.92-6.88 (m, 2H), 3.87 (s, 3H), 3.66 (s, 2H), 2.86-2.79 (m, 4H), 2.56 (s, 5H), 2.41 (s, 3H) ppm.

Workup

  1. customThe reaction was quenched with water (0.04 mL)
  2. stirringstirred for 110 minutes
  3. additionA 15% sodium hydroxide solution (0.04 mL) was added
  4. stirringstirred for 10 minutes
  5. additionwater (0.12 mL) was added
  6. stirringstirred for 10 minutes
  7. filtrationThe resultant solids were filtered
  8. washwashed with chloroform (10 mL)
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customThe resulted residue was purified by silica gel column chromatography, (3% methanol/chloroform)

Sources & evidence

ORD record
ord-6af0f63bb2b847439c77a821783a58db
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

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