4-Methylmorpholine → N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)furo[2,3-b]pyridine-2-carboxamide

HRID 931388ノート

反応式

HRID 931388 の反応式
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[C:12]3[CH:18]=[C:17]([C:19]([OH:21])=O)[O:16][C:13]3=[N:14][CH:15]=2)=[CH:5][CH:4]=1.[Br:24][C:25]1[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.CN(C)C(Cl)=[N+](C)C>CN(C=O)C>[Br:24][C:25]1[C:26]([NH:31][C:19]([C:17]2[O:16][C:13]3=[N:14][CH:15]=[C:10]([CH2:9][O:8][CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=4)[CH:11]=[C:12]3[CH:18]=2)=[O:21])=[N:27][CH:28]=[CH:29][CH:30]=1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 8177002-Amino-3-bromopyridineHCID 10989639Chloro-N,N,N',N'-tetramethylformamidinium HexafluorophosphateHCID 900505445-(((4-Methoxybenzyl)-oxy)methyl)furo[2,3-b]pyridine-2-carboxylic acid

生成物 1

HCID 90050548N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)furo[2,3-b]pyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

In an oven-dried sealed tube, a mixture of 5-(((4-methoxybenzyl)-oxy)methyl)furo[2,3-b]pyridine-2-carboxylic acid (2.0 g, 6.4 mmol), 3-bromo-2-amino pyridine (3.31 g, 19.2 mmol), N-methyl morpholine (1.93 g, 19.2 mmol) and N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (3.58 g, 12.8 mmol) in DMF (20 mL) was heated to 70° C. for 5 h. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether to give the title compound. MS: m/z=468.5 (M+1).

後処理

  1. customIn an oven-dried sealed tube
  2. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-2cdc9a834ef840699759a548ccfcb69e
出典データセット
uspto-grants-2016_03
特許番号
US09296750B2

反応ノート

読み込み中…