Water → HCID 68886419, compound

HRID 917667Notes

Reaction equation

HRID 917667 reaction equation
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)#[C-:2].[CH3:23][C:24]1[N:29]=[C:28]([CH:30]=[O:31])[CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O>CO.C(Cl)Cl>[O:8]1[C:7]2[CH:11]=[CH:12][C:4]([C:3]3[N:1]=[CH:2][O:31][C:30]=3[C:28]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:23])[N:29]=3)=[CH:5][C:6]=2[O:10][CH2:9]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 27717375-[Isocyano(4-methylbenzene-1-sulfonyl)methyl]-2H-1,3-benzodioxole

Product 1

HCID 68886419HCID 68886419, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-[isocyano-(toluene-4-sulfonyl)-methyl]-benzo[1,3]dioxole (40 mg, 0.127 mmol), 6-methyl-pyridine-2-carbaldehyde (15.4 mg, 0.127 mmol, 1 equiv) and potassium carbonate (26 mg, 0.19 mmol, 1.5 equiv) in methanol (1 mL) was shaken at 70° C. for 2 hours. The reaction mixture was concentrated in vacuo, and resulting residue was partitions between water (1 mL) and methylene chloride (1 mL). The organics were purified by silica gel chromatography (20% acetone in hexane) to provide 2-(4-Benzo[1,3]dioxol-5-yl-oxazol-5-yl)-6-methyl-pyridine as a colorless oil (8 mg, 22%) [LCMS: Rt-2.34 min; M+H=281.2].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customresulting residue
  3. customThe organics were purified by silica gel chromatography (20% acetone in hexane)

Sources & evidence

ORD record
ord-750f6e2c84254be7a3b38ce02962bfa3
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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