Acetic Acid → HCID 22626773, compound

HRID 277964Notes

Reaction equation

HRID 277964 reaction equation
[C:1]1([C:7]2[N:11]3[CH:12]=[C:13]([C:16](=[O:21])N(C)OC)[CH:14]=[CH:15][C:10]3=[N:9][C:8]=2[N:22]2[Si](C)(C)CC[Si]2(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:31]([Mg]Cl)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CO.C(O)(=O)C>C1COCC1>[NH2:22][C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:21])[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:12][N:11]2[C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 22626733HCID 22626733, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 22626773HCID 22626773, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The N-(3-phenyl-6-[N-methyl-N-methoxycarbamoyl]imidazo[1,2-a]pyridin-2-yl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane (812 mg, 4 mmol) was dissolved in 30 ml of THF under N2 and benzylmagnesiumchloride (2 M in THF, 6 ml, 12.0 mmol) was added. The mixture was allowed to stir for 18 hours at RT before adding 15 ml of MeOH and 3 ml of acetic acid. The mixture was allowed to stir for 1 hour at RT. The solvents were removed in vacuo and the residue taken up in 400 ml of EtOAc and 60 ml of NaHCO3. The EtOAc was separated and washed with with brine (2×75 ml), dried over NaSO4, and then concentrated in vacuo. The residue was purified by normal phase flash chromatography (EtOAc). The product fractions were recrystalized from EtOAc to yield 398 mg of product. (31.6%). MS(FD), NMR.

Workup

  1. stirringto stir for 1 hour at RT
  2. customThe solvents were removed in vacuo
  3. customThe EtOAc was separated
  4. washwashed with with brine (2×75 ml)
  5. dry with materialdried over NaSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by normal phase flash chromatography (EtOAc)
  8. customThe product fractions were recrystalized from EtOAc

Sources & evidence

ORD record
ord-7c2ac91ecbf44ca4a9dd5a842e8fdae1
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

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