Aluminium lithium hydride → HCID 22479815, compound

HRID 1349607Notes

Reaction equation

HRID 1349607 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=O)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][CH2:18][C:20]4[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 22479938HCID 22479938, compound

Product 1

HCID 22479815HCID 22479815, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-[3-(4-fluorophenyl)(1H-indazol-5-yl)]-4-pyridylcarboxamide (50 mg, 0.12 mmol) in THF (3 mL) was added lithium aluminum hydride (LAH) (9 mg, 0.24 mmol). The solution was stirred for 3 hours when an additional equivalence of LAH was added. The reaction was stirred for another 3 hours when it was quenched with ethyl acetate and water (100 mL) was added. The layers were separated and the water layer extracted with ethyl acetate (3×30 mL). The combined organic layers were dried (Na2SO4) and concentrated to an oil. The oil was taken up in methanol (10 mL) and 6N HCl (10 mL) and heated to 80° C. for 2 hours when it was quenched with NaHCO3 and extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated to afford the title compound (7.5 mg, 20% yield). 1H NMR (CDCl3) δ 8.6 (br s, 1H), 7.76 (dd, 2H), 7.35 (d, 2H), 7.24 (d, 2H), 7.15 (t, 2H), 6.9–6.8 (m, 2H), 4.43 (s, 2H); ES-MS (m/z) 319 [M+1]+.

Workup

  1. additionwas added
  2. customwas quenched with ethyl acetate and water (100 mL)
  3. additionwas added
  4. customThe layers were separated
  5. extractionthe water layer extracted with ethyl acetate (3×30 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated to an oil
  8. customwas quenched with NaHCO3
  9. extractionextracted with ethyl acetate
  10. dry with materialThe combined organic layers were dried (Na2SO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-705b2e43d7e449fc9bdfb3487ff5ecb5
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…