Lithium triethylborohydride → 2-Ethyl-8-methylbenzo[f][1,7]naphthyridin-5-amine

HRID 1259116Notes

Reaction equation

HRID 1259116 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([C:12](OCC)=O)=[CH:7][C:6]=2[C:5]2[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:4]=2[N:3]=1.[Li+].[B-](CC)(CC)[CH2:24]C>C1COCC1>[CH2:12]([C:8]1[CH:9]=[N:10][C:11]2[C:6]([CH:7]=1)=[C:5]1[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:4]1=[N:3][C:2]=2[NH2:1])[CH3:24]

Participants

4

Reactant 2

HCID 23712863Lithium triethylborohydrideHCID 58213495Ethyl 5-amino-8-methylbenzo[f][1,7]naphthyridine-2-carboxylate

Product 1

HCID 582135882-Ethyl-8-methylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of ethyl 5-amino-8-methylbenzo[f][1,7]naphthyridine-2-carboxylate (from the previous step) in THF (0.2 M) cooled in an ice-water bath was added 1 N solution of super hydride in THF (10 eq.). Upon completion of the reaction the reaction was quenched with 1 N HCl, and extracted with EtOAc. Combined organic extracts were concentrated en vaccuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)methanol as a white solid. 1H NMR (CDCl3): δ 8.68 (d, 1H), 8.52 (d, 1H), 8.04 (d, 1H), 7.44 (s, 1H), 7.12 (dd, 1H), 6.00 (bs, 2H), 4.90 (s, 2H), 2.45 (s, 3H). LRMS [M+H]=240.1

Workup

  1. customUpon completion of the reaction the reaction
  2. customwas quenched with 1 N HCl
  3. extractionextracted with EtOAc
  4. concentrationCombined organic extracts were concentrated en vaccuo

Sources & evidence

ORD record
ord-fd4efb736368448eaa9b4f79cc56507e
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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