Aluminium lithium hydride → HCID 24887414, compound

HRID 1785393Notes

Reaction equation

HRID 1785393 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([CH3:21])([CH3:20])[C:18]#[N:19])=[CH:16][C:11]3=[N:10][C:9]=2[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:5]=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:19][CH2:18][C:17]([C:15]1[CH:14]=[CH:13][N:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=3)=[C:9]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[N:10]=[C:11]2[CH:16]=1)([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69055968HCID 69055968, compound

Product 1

HCID 24887414HCID 24887414, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100 mL round bottom flask containing nitrile 27 (700 mg, 1.88 mmol) in THF (25 mL) was charged with lithium aluminum hydride (285 mg, 7.52 mmol). After stirring at room temperature for 45 minutes, the reaction mixture was poured into an 1.0 L Erlenmeyer flask and quenched with 200 mL ethyl acetate, 10 mL water, sodium sulfate, and an excess of 2:1 Na2SO4 10H2O:celite. The mixture was filtered, then concentrated under reduced pressure, and then dissolved in a minimum volume of CH2Cl2, then loaded onto a 40 g Isco RediSep normal phase silica cartridge, and purified on an Isco OptiX10 CombiFlash instrument using a gradient that started at 100% methylene chloride and ended at 90% methylene chloride, 9% methanol, 1% concentrated ammonium hydroxide. Fractions containing desired product were pooled and concentrated under reduced pressure. Yield of 28: 196 mg (28%). 1H NMR (500 MHz, CDCl3) δ 1.38 (s, 6H), 2.89 (s, 2H), 5.14 (bs, 2H), 6.54 (d, J=5.5 Hz, 1H), 6.97 (dd, J=7.5, 2.0 Hz, 1H), 7.14 (m, 2H), 7.65 (m, 3H), 8.13 (d, J=5.5 Hz, 1H), 9.46 (dd, J=7.5, 0.5 Hz, 1H). MS (ESI+) 377.2.

Workup

  1. additionthe reaction mixture was poured into an 1.0 L Erlenmeyer flask
  2. customquenched with 200 mL ethyl acetate, 10 mL water, sodium sulfate
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. dissolutiondissolved in a minimum volume of CH2Cl2
  6. custompurified on an Isco OptiX10 CombiFlash instrument
  7. additionFractions containing desired product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d2d6b95e52b4676820828501ae92e52
Source dataset
uspto-grants-2009_03
Patent number
US07504501B2

Reaction notes

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