5-Aminobenzo[f][1,7]naphthyridine-8-carbaldehyde → 1-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanol

HRID 340302Notes

Reaction equation

HRID 340302 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([CH:16]=[O:17])=[CH:15][C:4]=2[N:3]=1.[Li][CH3:19]>C1COCC1>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([CH:16]([OH:17])[CH3:19])=[CH:15][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 866523555-Aminobenzo[f][1,7]naphthyridine-8-carbaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 582136971-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-aminobenzo[f][1,7]naphthyridine-8-carbaldehyde (from Example 87) (1.0 eq.) in THF (0.02M) was added MeLi (2.5 eq.) at −78° C. The reaction was allowed to warm to ambient temperature overnight. The reaction was quenched by saturated NH4Cl and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4 and concentrated en vacuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give 145-aminobenzo[f][1,7]naphthyridin-8-yl)ethanol as a yellow solid: 1H NMR (methanol-d4): δ 8.94 (dd, 1H), 8.88 (dd, 1H), 8.38 (d, 1H), 7.81 (dd, 1H), 7.62 (d, 1H), 7.41 (dd, 1H), 4.97 (q, 1H), 1.53 (d, 3H). LRMS [M+H]=240.1.

Workup

  1. customThe reaction was quenched by saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated en vacuo
  6. customto obtain a crude residue
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  8. customto give 145-aminobenzo[f][1,7]naphthyridin-8-yl)ethanol as a yellow solid

Sources & evidence

ORD record
ord-8ff660522b7d44b9bb1a23c8a2626356
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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