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

HRID 1479588ノート

反応式

HRID 1479588 の反応式
[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

参加物

4

反応物 2

HCID 866523555-Aminobenzo[f][1,7]naphthyridine-8-carbaldehydeHCID 178418348HCID 178418348、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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 vaccuo 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 1-(5-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.

後処理

  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 vaccuo
  6. customto obtain a crude residue
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

出典と根拠

ORDレコード
ord-9108e42e8eb8455888b686ca99258d05
出典データセット
uspto-grants-2016_08
特許番号
US09408907B2

反応ノート

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