2-Fluoroaniline → HCID 59026788, compound

HRID 658393Notes

Reaction equation

HRID 658393 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14].[Br:19][C:20]1[CH:28]=[N:27][CH:26]=[C:25](F)[C:21]=1[C:22]([OH:24])=[O:23]>C1COCC1>[Br:19][C:20]1[CH:28]=[N:27][CH:26]=[C:25]([NH:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[F:11])[C:21]=1[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 95842-FluoroanilineHCID 2733832Lithium HexamethyldisilazideHCID 509904913-Bromo-5-fluoropyridine-4-carboxylic acid

Product 1

HCID 59026788HCID 59026788, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (54.6 mL, 1.0 M in THF, 54.6 mmol) was added to a solution of 2-fluoro aniline (3.5 mL, 36.4 mmol) in THF (100 mL) at −78° C. The resulting solution was for 1 h at −78° C. 3-Bromo-5-fluoro-isonicotinic acid (1) (4.0 g, 18.2 mmol) was added as a solid, and the reaction solution was stirred for 48 h at room temperature. The reaction solution was concentrated via rotary evaporation, diluted with satd. NaHCO3, and washed with EtOAc. The aqueous solution was acidified with concentrated HCl. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to afford the desired product (4.2 g, 74%) as a yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated via rotary evaporation
  2. additiondiluted with satd
  3. washNaHCO3, and washed with EtOAc
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with H2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d0f8b83f382e40cc9581ca5ec792bd47
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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