Aluminium lithium hydride → HCID 76852932, compound

HRID 1821912Notes

Reaction equation

HRID 1821912 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([C:17](OCC)=[O:18])[NH:14][C:11]2=[CH:12][N:13]=1>O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([CH2:17][OH:18])[NH:14][C:11]2=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44630703Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 76852932HCID 76852932, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (105 mg, 2.77 mmol) was added in three portions to a solution of ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (410 mg, 1.83 mmol) in tetrahydrofuran (15 mL) under stirring at 0° C. under a nitrogen atmosphere. The reaction mixture was warmed to room temperature and then heated to 60° C. for 3 h. The reaction mixture was quenched by the gradual addition of hydrated sodium sulfate. The sodium sulfate was removed by filtration and washed thoroughly with tetrahydrofuran to give a yellow filtrate, which was concentrated to a brown solid. After sonication in diethyl ether for 20 minutes, the solid was collected by filtration and dried to give (5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (225 mg, 67%) as a brown solid: 1H NMR (300 MHz, Acetone-d6) δ4.52-4.89 (3H, m), 6.38 (1H, s), 7.47 (1H, s), 8.49 (1H, s), 10.88 (1H, br s).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. temperatureheated to 60° C. for 3 h
  3. customThe reaction mixture was quenched by the gradual addition of hydrated sodium sulfate
  4. customThe sodium sulfate was removed by filtration
  5. washwashed thoroughly with tetrahydrofuran
  6. customto give a yellow filtrate, which
  7. concentrationwas concentrated to a brown solid
  8. customAfter sonication in diethyl ether for 20 minutes
  9. filtrationthe solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-0bbe0f0394154f92b951f2dd2f6d5305
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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