Sodium hydride → HCID 71238252, compound

HRID 340073Notes

Reaction equation

HRID 340073 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[NH:14][C:15]([I:17])=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:20][Si:21]([CH2:24][CH2:25][O:26][CH2:27]Cl)([CH3:23])[CH3:22]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH2:27][O:26][CH2:25][CH2:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[C:15]([I:17])=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178451661HCID 178451661, compound

Product 1

HCID 71238252HCID 71238252, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-iodo-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester (Preparation 21, 17.25 g, 49.4 mmol) in THF (250 mL) was added NaH (60% in paraffin oil, 2.08 g, 51.9 mmol) and the resulting solution was stirred at room temperature for 1.5 hours. The reaction mixture was cooled to 0° C. and SEM-Cl (9.18 mL, 51.9 mmol) was added dropwise. The reaction was stirred at room temperature for 18 hours, cooled to 0° C. and quenched carefully with water (500 mL). The resulting solution was extracted with EtOAc (2×500 mL) and the combined organics layers were dried over MgSO4, filtered through a pad of silica and concentrated in vacuo to give the title compound (23.4 g) in a 99% yield.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe reaction was stirred at room temperature for 18 hours
  3. temperaturecooled to 0° C.
  4. customquenched carefully with water (500 mL)
  5. extractionThe resulting solution was extracted with EtOAc (2×500 mL)
  6. dry with materialthe combined organics layers were dried over MgSO4
  7. filtrationfiltered through a pad of silica
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d094e5fcd35c41258da1d31d6d893f77
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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