Dimethylformamide → HCID 178427346, compound

HRID 75033Notes

Reaction equation

HRID 75033 reaction equation
[F:1][C:2]1[CH:7]=[N:6][C:5]2[NH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[OH:11].[C:12]1(C)[C:13]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1.[H-].[Na+].[CH3:25]N(C=O)C>>[F:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([S:18]([C:13]3[CH:12]=[CH:17][C:16]([CH3:25])=[CH:15][CH:14]=3)(=[O:19])=[O:20])[CH:9]=[CH:10][C:4]=2[C:3]=1[OH:11]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8623o-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178516672HCID 178516672, compound

Product 1

HCID 178427346HCID 178427346, compound

Conditions

Temperature
45 °C

Procedure

To a solution of 5-fluoro-1H-pyrrolo[2,3-b]pyridin-4-ol (1.2 g, 7.9 mmol) in 80 mL DMF at 0° C. was added toluenesulfonyl chloride (1.8 g, 9.5 mmol) followed by NaH (0.8 g, 19.7 mmol, 60% w/w). The reaction was slowly warmed to 45° C. after 3 hours and stirred for an additional 3 hours. The mixture was then concentrated in vacuo. The crude oil was dissolved in 100 mL EtOAc and washed with water (2×50 mL) and brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (10% EtOAc/Hexanes) to afford 1.5 g of the desired product.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutionThe crude oil was dissolved in 100 mL EtOAc
  3. washwashed with water (2×50 mL) and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified via silica gel chromatography (10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-817935913f814136b21113670dd0ace8
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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