Aluminium lithium hydride → HCID 57588508, compound

HRID 1782106Notes

Reaction equation

HRID 1782106 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([N:12]3[C:16]4[CH:17]=[C:18]([C:20](OCC)=[O:21])[NH:19][C:15]=4[N:14]=[CH:13]3)[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([N:12]3[C:16]4[CH:17]=[C:18]([CH2:20][OH:21])[NH:19][C:15]=4[N:14]=[CH:13]3)[CH:9]=[CH:10][CH:11]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68870046HCID 68870046, compound

Product 1

HCID 57588508HCID 57588508, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of ethyl 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (300 mg, 0.89 mmol) in dry THF (9 mL) was added lithium aluminum hydride (1.07 mL, 1.07 mmol, 1.0 M in THF) dropwise at −40° C. under nitrogen. The resulting solution was allowed to slowly warm to −20° C. over the course of 1 hour after which time the reaction was quenched with saturated aqueous ammonium chloride (3 mL) and diluted with ethyl acetate (40 mL). The suspension was filtered through Celite, the filtrate washed with saturated aqueous sodium chloride (20 mL) and then dried over anhydrous sodium sulfate and concentrated in vacuo. The crude material thus isolated was chromatographed over silica gel eluting with MeOH:CH2Cl2 0%→1%→2%) to furnish 40.6 mg (15.5%) of [1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazol-5-yl]methanol EXAMPLE 5. 1H NMR (400 MHz, CDCl3): δ=9.46 (s, 1H), 7.76 (s, 1H), 7.67 (t, J=2.0 Hz, 1H), 7.51-7.49 (m, 1H), 7.47-7.45 (m, 1H), 7.44-7.41 (m, 2H), 7.39-7.35 (m, 2H), 6.16 (d, J=1.2 Hz, 1H), 4.75 (s, 2H). MS (ES+): m/z 296.17 (100) [MH+].

Workup

  1. customwas quenched with saturated aqueous ammonium chloride (3 mL)
  2. additiondiluted with ethyl acetate (40 mL)
  3. filtrationThe suspension was filtered through Celite
  4. washthe filtrate washed with saturated aqueous sodium chloride (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude material thus isolated
  8. customwas chromatographed over silica gel eluting with MeOH

Sources & evidence

ORD record
ord-1db183c7ce8e43e3853e245c13d60224
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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