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

HRID 453062

반응식

HRID 453062 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-01736928d2b048e1b0e4f8a8a2b11764
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492408B2

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