Aluminium lithium hydride → HCID 59732469, compound

HRID 131520Notes

Reaction equation

HRID 131520 reaction equation
CO[C:3](=O)[NH:4][C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=3)[N:11]([CH2:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:8]2=[N:9][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:12]2[N:11]([CH2:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:8]3=[N:9][CH:10]=[C:5]([NH:4][CH3:3])[CH:6]=[C:7]3[CH:13]=2)=[CH:16][CH:17]=1)[CH3:23]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59732478HCID 59732478, compound

Product 1

HCID 59732469HCID 59732469, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-[(4-ethoxyphenyl)methyl]-1-[(tetrahydro-2H-pyran-4-yl)methyl]-1H-pyrrolo[2,3-b]pyridin-5-yl]-carbamic acid methyl ester (153 mg, 0.36 mmol) in THF (25 ml) at 0° C. was added lithium aluminum hydride (35 mg, 0.90 mmol). The mixture was stirred for 48 hours at room temperature. The reaction was then cooled to 0° C. and quenched by dropwise addition of water (35 □L), followed by 4M NaOH aqueous solution (35 μL) and water (105 μL). After stirring at room temperature for 30 minutes, the suspension was filtered over Diatomaceous earth and concentrated in vacuo to give 100 mgs of colorless oil. 1H NMR (400 MHz, CHLOROFORM-D) δ 1.40 (m, 5 H), 1.59 (m, 2 H), 2.05 (m, 1 H), 2.87 (s, 3 H), 3.36 (m, 2 H), 3.66 (m, 2 H), 4.01 (m, 6 H), 5.99 (s, 1 H), 6.83 (d, J=8.79 Hz, 2 H), 6.98 (s, 1 H), 7.05 (d, J=2.54 Hz, 1 H), 7.10 (d, J=8.79 Hz, 2 H), 7.79 (d, J=2.54 Hz, 1 H). MS (ESI) (M+H)+: 380.

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. customquenched by dropwise addition of water (35 □L)
  3. stirringAfter stirring at room temperature for 30 minutes
  4. filtrationthe suspension was filtered over Diatomaceous earth
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-676051fb4356435f8e619eabd4df7b06
Source dataset
uspto-grants-2008_06
Patent number
US07384955B2

Reaction notes

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