Sodium Bicarbonate → HCID 69332384, compound

HRID 2370943Notes

Reaction equation

HRID 2370943 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[C:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[N:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[N:36][CH:37]=1.[C:46]([O-])(O)=O.[Na+]>C1COCC1.CC(=O)OCC>[C:41]([O:40][C:39]([NH:38][C:35]1[N:36]=[CH:37][C:32]([CH2:31][CH:15]([C:13]2[N:12]=[CH:11][N:10]([S:7]([C:1]3[CH:2]=[CH:3][C:4]([CH3:46])=[CH:5][CH:6]=3)(=[O:8])=[O:9])[CH:14]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:33][CH:34]=1)=[O:45])([CH3:44])([CH3:43])[CH3:42]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamateHCID 86612814HCID 86612814, compound

Product 1

HCID 69332384HCID 69332384, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.00 g (3.39 mmol) of methyl (1-benzenesulfonyl-1H-imidazol-4-yl)acetate (example 1d) in 100 ml of THF was cooled to −78° C. and 3.74 ml (3.74 mmol, 1M in THF) of lithium bis(trimethylsilyl)amide were added in three portions over the course of 3 min. The mixture was stirred at this temperature for 5 min and then 0.65 g (2.26 mmol) of tert-butyl (5-bromomethylpyridin-2-yl)carbamate (example 1b) was added in one portion. The mixture was stirred at −78° C. for 1 h and then allowed to reach RT. The mixture was poured into a mixture of EA and saturated NaHCO3 solution. After shaking, the organic phase was separated off, dried over Na2SO4, filtered and concentrated to dryness. The residue was recrystallized from EA/heptane. The resulting crystals were filtered off with suction, washed with a little EA and heptane and dried. 0.66 g of the title compound was obtained.

Workup

  1. stirringThe mixture was stirred at −78° C. for 1 h
  2. customto reach RT
  3. stirringAfter shaking
  4. customthe organic phase was separated off
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was recrystallized from EA/heptane
  9. filtrationThe resulting crystals were filtered off with suction
  10. washwashed with a little EA and heptane
  11. customdried

Sources & evidence

ORD record
ord-e2c69905c1414547ab6b64312dc4e7d1
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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