Sodium hydride → HCID 90413560, compound

HRID 1522022Notes

Reaction equation

HRID 1522022 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[C:11]([I:12])[C:3]=12.[H-].[Na+].Cl[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21]>O1CCCC1>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=[C:11]([I:12])[C:3]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 497616274-Chloro-5-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 90413560HCID 90413560, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 263A (2.8 g, 9.44 mmol) in tetrahydrofuran (200 mL) was cooled to 0° C. and sodium hydride (0.34 g, 14.17 mmol) was added. The mixture was stirred at 0° C. for 30 minutes and (2-(chloromethoxy)ethyl)trimethylsilane (2.5 mL, 14.17 mmol) was added. The mixture was warmed to room temperature, stirred for 2 hours, quenched with brine and extracted with ethyl acetate (twice). The organic phase was concentrated and purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound. MS (ESI+) m/z 427 (M+H)+.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 2 hours
  3. customquenched with brine
  4. extractionextracted with ethyl acetate (twice)
  5. concentrationThe organic phase was concentrated
  6. custompurified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-085c445966b64965a11a1f0267fd5b05
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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