Pyridine → 3-bromo-1-(tert-butyldimethylsilyl)-5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 493150Notes

Reaction equation

HRID 493150 reaction equation
[Br:1]Br.[C:3]([Si:7]([CH3:25])([CH3:24])[N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[CH:16]=[C:11]2[CH:10]=[CH:9]1)([CH3:6])([CH3:5])[CH3:4].N1C=CC=CC=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[Br:1][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[CH:16]=2)[N:8]([Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:25])[CH3:24])[CH:9]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 22607107sodium thiosulfate NaHCO3HCID 497590641-(tert-Butyl-dimethyl-silanyl)-5-(3-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 576811263-bromo-1-(tert-butyldimethylsilyl)-5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridineYield 95.8%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

A solution of Br2 (1.12 mL, 21.8 mmol) in CCl4 was added dropwise to a stirred and cooled (0° C.) solution of 8 (7.10 g, 21.8 mmol) and pyridine (2.1 mL, 26.2 mmol) in dry CHCl3 (330 mL). Progress of the reaction was followed by TLC. When the reaction was completed, aqueous NaHCO3—Na2S2O3 solution was added. The organic solution was separated and the aqueous layer was extracted with CH2Cl2 (3×100 mL). Combined organic solutions were dried (MgSO4), concentrated and purified by SGC with hexane:benzene as eluent in gradient (up to 14% benzene) to afford 9 (8.47 g, 91%) as tan solid. 1H NMR (400 MHz, CDCl3) δ 0.65 (s, 6H), 0.97 (s, 9H), 7.02-7.10 (m, 1H), 7.29 (s, 1H), 7.33-7.38 (m, 1H), 7.40-7.47 (m, 2H), 7.97 (d, J=2.2 Hz, 1H), 8.51 (d, J=2.2 Hz, 1H).

Workup

  1. customThe organic solution was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  3. dry with materialCombined organic solutions were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by SGC with hexane

Sources & evidence

ORD record
ord-07c2f4b6f0f24ecebe908cbb5e1749b3
Source dataset
uspto-grants-2009_05
Patent number
US07534800B2

Reaction notes

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