Dimethylformamide → HCID 68554352, compound

HRID 2382126Notes

Reaction equation

HRID 2382126 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1.C[N:14](C=O)C>>[F:3][C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][N:10]([NH2:14])[C:7]2=[N:8][CH:9]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 207844625-Fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68554352HCID 68554352, compoundYield 88%

Conditions

Temperature
0 °C

Procedure

A suspension of NaH (4.4 g, 110 mmol, 60% in mineral oil) in DMF (37 mL) at 0° C. is treated with 5-fluoro-1H-pyrrolo[2,3-b]pyridine (1.0 g, 7.4 mmol) and stirred at 0° C. for 1 h. The mixture is treated with HOSA (4.2 g, 37 mmol) portion wise and warmed to rt over 2 h. The mixture is then poured over ice, filtered through a pad of Celite, and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 30%-70% EtOAc in heptane to afford 5-fluoro-pyrrolo[2,3-b]pyridin-1-ylamine (980 mg, 88%). MS: 152 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.20 (s, 1H), 7.60 (m, 1H), 7.42 (m, 1H), 6.36 (s, 1H), 5.01 (s, NH2, 2H).

Workup

  1. additionThe mixture is treated with HOSA (4.2 g, 37 mmol) portion wise
  2. temperaturewarmed to rt over 2 h
  3. additionThe mixture is then poured over ice
  4. filtrationfiltered through a pad of Celite
  5. extractionextracted with EtOAc (3×50 mL)
  6. dry with materialThe combined organic layer is dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by silica gel chromatography
  10. washeluting with 30%-70% EtOAc in heptane

Sources & evidence

ORD record
ord-fb1868994d0c44ec8d9676b661d89573
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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