2-Methoxypyrimidine-5-carboxaldehyde → 3-[5-(2-{(2-methoxyethyl)[(2-methoxy-5-pyrimidinyl)methyl]amino}ethoxy)-1H-indol-2-yl]-2(1H)-quinolinone

HRID 1007638ノート

反応式

HRID 1007638 の反応式
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]1[C:19](=[O:28])[NH:20][C:21]3[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:12]2.[CH3:29][O:30][C:31]1[N:36]=[CH:35][C:34]([CH:37]=O)=[CH:33][N:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:37][C:34]1[CH:33]=[N:32][C:31]([O:30][CH3:29])=[N:36][CH:35]=1)[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]1[C:19](=[O:28])[NH:20][C:21]3[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:12]2

参加物

5

反応物 3

HCID 31518662-Methoxypyrimidine-5-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 99077363-(5-{2-[(2-methoxyethyl)amino]ethoxy}-1H-indol-2-yl)-2(1H)-quinolinone

生成物 1

HCID 98272683-[5-(2-{(2-methoxyethyl)[(2-methoxy-5-pyrimidinyl)methyl]amino}ethoxy)-1H-indol-2-yl]-2(1H)-quinolinone

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

A solution of 3-5-{2-[(2-methoxyethyl)amino]ethoxy}-1H-indol-2-yl)-2(1H) -quinolinone 2-1 (150 mg, 0.4 mmol), 2-methoxypyrimidine-5-carboxaldehyde (110 mg, 0.8 mmol) and sodium triacetoxyborohydride (168 mg, 0.8 mmol) in DCE (25 mL) was stirred under ambient conditions for 18 h. The reaction mixture was concentrated, and the residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was suspended in ethyl ether with the aid of sonication, then filtered and air dried to provide 3-[5-(2-{(2-methoxyethyl)[(2-methoxy-5-pyrimidinyl) methyl]amino}ethoxy)-1H-indol-2-yl]-2(1H)-quinolinone (2-2) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 11.05 (s, 1H), 9.60 (s, 1H), 8.53 (s, 2H), 8.33 (s, 1H), 7.68 (d, 1H, J=8 Hz), 7.52 (t, 1H, J=8 Hz), 7.34 (d, 1H, J=8 Hz), 7.27 (t, 1H, J=8 Hz), 7.22 (d, 1H, J=8 Hz), 7.05 (s, 1H), 6.96 (s, 1H), 6.86 (dd, 1H, J=8, 2 Hz), 4.13 (t, 2H, J=6 Hz), 4.01 (s, 3H), 3.80 (s, 2H), 3.53 (t, 2H, J=6 Hz), 3.34 (s, 3H), 3.01 (t, 2H, J=6 Hz), 2.84 (t, 2H, J=6 Hz).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc and saturated NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was suspended in ethyl ether with the aid of sonication
  7. filtrationfiltered
  8. customair dried

出典と根拠

ORDレコード
ord-0323309929614b71b3cd288939b057f0
出典データセット
uspto-grants-2004_09
特許番号
US06794393B1

反応ノート

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