Water → HCID 86694700, compound

HRID 475118Notes

Reaction equation

HRID 475118 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([Si](CCC)(CCC)CCC)[CH:6]=[CH:5][C:4]=2[C:3]=1[C:21]([OH:23])=O.F[P-](F)(F)(F)(F)F.[N:31]1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.O.N.O>CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:21]([NH2:31])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12896473Azane;hydrateHCID 71272430HCID 71272430, compound

Product 1

HCID 86694700HCID 86694700, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-fluoro-1-(tripropylsilyl)-1H-indole-4-carboxylic acid (500 mg, 1.49 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (851 mg, 2.24 mmol), and TEA (452 mg, 4.48 mmol) in DMF (5 mL) was stirred at RT for 1 hour. To the mixture was added ammonia water (1 mL), followed by stirring at RT overnight. The reaction mixture was poured into water (100 mL) and extracted with EtOAc (50 mL×3). The combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography using petroleum ether/EtOAc (2:1) as eluting solvents to afford 5-fluoro-1H-indole-4-carboxamide as a white solid (260 mg, 52.2%). MS (ESI): m/z=179.2 [M+1]+.

Workup

  1. stirringby stirring at RT overnight
  2. extractionextracted with EtOAc (50 mL×3)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by SiO2 chromatography
  8. washas eluting solvents

Sources & evidence

ORD record
ord-d84f140928714a388d5411b89b7b97e8
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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