Aluminium lithium hydride → HCID 24826338, compound

HRID 910958Notes

Reaction equation

HRID 910958 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:18]=[C:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[C:11]([C:12](OCC)=[O:13])=[CH:10][N:9]=2)[S:5][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[N:9]=[CH:10][C:11]([CH2:12][OH:13])=[C:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=[CH:22][CH:21]=3)[CH:18]=2)[S:5][CH:6]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 24825976HCID 24825976, compound

Product 1

HCID 24826338HCID 24826338, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinate (1.50 g, 3.70 mmol) in THF (15 mL) was added to a 1.0 M solution of lithium aluminum hydride (18.5 mL, 18.5 mmol) in ether at 0° C. and stirred for 30 minutes. The reaction was quenched with sodium sulfate decahydrate, stirred 30 minutes, and filtered. The solids were washed with THF, filtered, and concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried, and concentrated. The residue was triturated with hexanes and filtered to afford (6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)pyridin-3-yl)methanol (1.10 g, 81.8% yield) as a white solid. 1H NMR (DMSO-d6) δ 10.68 (bs, 1H), 8.25 (s, 1H), 8.05 (d, 1H), 7.92 (d, 2H), 7.53-7.64 (m, 3H), 7.36 (d, 1H), 6.47 (s, 1H), 6.19 (s, 1H), 5.20 (t, 1H), 4.71 (d, 2H), 2.13 (s, 3H); Mass spectrum (esi) m/z=364 (100) (M+H).

Workup

  1. customThe reaction was quenched with sodium sulfate decahydrate
  2. stirringstirred 30 minutes
  3. filtrationfiltered
  4. washThe solids were washed with THF
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was partitioned between ethyl acetate and water
  8. washThe organic layer was washed with brine
  9. customdried
  10. concentrationconcentrated
  11. customThe residue was triturated with hexanes
  12. filtrationfiltered

Sources & evidence

ORD record
ord-1d39a2a4e24a42de915e54051c96f78d
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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