Sodium hydride → 4-(2-Bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl ester

HRID 453062

反応式

HRID 453062 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17](F)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1>C1COCC1>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=2)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 3464554-Amino-2-bromopyridineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

生成物 1

HCID 866585844-(2-Bromo-pyridin-4-ylamino)-3-nitro-benzoic acid methyl ester収率 85.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-Bromo-pyridin-4-ylamine 2 (4.3 g; 25 mmol) and NaH 60% (1.5 g; 37 mmol) was at 0° C. stirred for 1 h in dry THF (50 ml) and then a solution of 4-Fluoro-3-nitro-benzoic acid methyl ester 1 (5 g; 25 mmol) in dry THF (50 ml) was addeddrop. The resulting cold solution was allowed to reach RT and stirred overnight for completion of the reaction. LCMS showed complete conversion to product and the reaction was quenched by addition of iPrOH and H2O. A precipitate was formed and this was filtered off, dried under educed pressure to obtain 3 as a yellow solid (7.5 g). Yield 85%. The product identity was confirmed by NMR and LCMS and taken for the next step.

後処理

  1. customwas at 0° C.
  2. customto reach RT
  3. customthe reaction was quenched by addition of iPrOH and H2O
  4. customA precipitate was formed
  5. filtrationthis was filtered off
  6. customdried

出典と根拠

ORDレコード
ord-01736928d2b048e1b0e4f8a8a2b11764
出典データセット
uspto-grants-2013_07
特許番号
US08492408B2

関連ノート

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