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

HRID 453062

Reaction equation

HRID 453062 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-01736928d2b048e1b0e4f8a8a2b11764
Source dataset
uspto-grants-2013_07
Patent number
US08492408B2

Linked notes

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