Hydrochloric Acid → 1H-Pyrrolo[2,3-B]pyridine-5-carboxaldehyde, 4-chloro-1-[tris(1-methylethyl)silyl]-

HRID 733069Notes

Reaction equation

HRID 733069 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:3]=12.[Li]C(CC)C.CN([CH:29]=[O:30])C.Cl.CCOCC.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:7]([CH:29]=[O:30])=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:18]([CH3:20])[CH3:19])[CH:12]([CH3:13])[CH3:14])[CH:9]=[CH:10][C:3]=12

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 114382724-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418400CID 53628100

Product 1

HCID 497590451H-Pyrrolo[2,3-B]pyridine-5-carboxaldehyde, 4-chloro-1-[tris(1-methylethyl)silyl]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (0.90 g, 2.91 mmol) in THF (8 mL), cooled at −78° C., is added slowly sec-BuLi (1.4 M in hexane, 4.16 mL, 5.82 mmol). After stirring for 45 minutes, the DMF (0.68 mL, 8.74 mmol) is added at −78° C. The mixture is stirred for 1 hour and quenched with HCl in ether solution (1M, 8.73 mL, 8.73 mmol). The mixture is allowed to warm to room temperature. The reaction mixture is basified with saturated sodium bicarbonate solution to a pH of 8 and extracted with ethyl acetate. The organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated to afford the mixture of the title compounds, which is used for next reaction without any further purification: MS m/z 337.2 (M+1).

Workup

  1. stirringThe mixture is stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford
  8. customis used for next reaction without any further purification

Sources & evidence

ORD record
ord-a009c0d9e7664c64b417f308191be083
Source dataset
uspto-grants-2009_09
Patent number
US07589101B2

Reaction notes

Loading…