Tetrahydrofuran → (3-amino-2,6-difluorophenyl)(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone

HRID 60115Notes

Reaction equation

HRID 60115 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([F:11])[C:3]=1[C:12]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([I:23])[CH:21]=2)[NH:16][CH:15]=1)=[O:13].C(OCC)(=O)C.O1CCCC1.C(=O)(O)[O-].[Na+]>O>[NH2:8][C:7]1[C:2]([F:1])=[C:3]([C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([I:23])[CH:21]=3)[NH:16][CH:15]=2)=[O:13])[C:4]([F:11])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 58368945(2,6-difluoro-3-nitrophenyl)(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone

Product 1

HCID 58368852(3-amino-2,6-difluorophenyl)(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanoneYield 87.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In a reaction vial, (2,6-difluoro-3-nitro-phenyl)-(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (45, 0.123 g, 0.287 mmol) is mixed with 5.0 mL of ethyl acetate and 5.0 mL of tetrahydrofuran. Stannous chloride, dehydrate (0.223 g, 0.989 mmol) is added and the reaction is heated at 60° C. for 24 hours. The reaction is poured into a mixture of 25 mL of water and 25 mL of saturated aqueous sodium bicarbonate and treated with celite, then filtered through a bed of celite. The celite is washed with ethyl acetate. The organic layer is separated and washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (46, 0.100 g). MS (ESI) [M+H+]+=399.9.

Workup

  1. additiontreated with celite
  2. filtrationfiltered through a bed of celite
  3. washThe celite is washed with ethyl acetate
  4. customThe organic layer is separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under vacuum
  9. customThe resulting material is purified by silica gel column chromatography
  10. washeluting with ethyl acetate and dichloromethane
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-79184add8a524334ba9ef07c7c76290c
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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