2-Bromopropane → HCID 68761810, compound

HRID 79584Notes

Reaction equation

HRID 79584 reaction equation
Br[CH:2]([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[F:11][C:12]1[C:17]([OH:18])=[CH:16][N:15]=[C:14]2[N:19]([Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:21][C:13]=12>CN(C=O)C>[F:11][C:12]1[C:17]([O:18][CH:2]([CH3:4])[CH3:3])=[CH:16][N:15]=[C:14]2[N:19]([Si:22]([CH:26]([CH3:28])[CH3:27])([CH:29]([CH3:31])[CH3:30])[CH:23]([CH3:24])[CH3:25])[CH:20]=[CH:21][C:13]=12

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 22273648HCID 22273648, compound

Product 1

HCID 68761810HCID 68761810, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromopropane (120 mg, 0.973 mmol) and potassium carbonate (448 mg, 3.24 mmol) were added to 4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol (200 mg, 0.648 mmol) in DMF (3 mL). The reaction was heated to 80° C. in a sealed tube for 18 hours and then cooled down. The reaction mixture was concentrated to dryness. The mixture was then suspended in DCM and filtered. The filtrate was concentrated and purified by chromatography (SP4, 12+M, water/ACN 80/20→10/90, 20CV) to yield 4-fluoro-5-isopropoxy-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (65 mg, 42%) as a solid.

Workup

  1. temperaturecooled down
  2. concentrationThe reaction mixture was concentrated to dryness
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by chromatography (SP4, 12+M, water/ACN 80/20→10/90, 20CV)

Sources & evidence

ORD record
ord-a753ab1f47c8474b82a450ef1307c7fe
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

Loading…