Diisopropylamine → HCID 67532332, compound

HRID 2388224Notes

Reaction equation

HRID 2388224 reaction equation
[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[C:5](I)=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(NC(C)C)(C)C.[Si:30]([C:34]#[CH:35])([CH3:33])([CH3:32])[CH3:31]>[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[C:5]([C:35]#[C:34][Si:30]([CH3:33])([CH3:32])[CH3:31])=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 86648126HCID 86648126, compound

Product 1

HCID 67532332HCID 67532332, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-hydroxy-4-iodo-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (500 mg, 1.22 mmol), copper iodide (93 mg, 0.49 mmol), and PdCl2(PPh3)2 (171 mg, 0.24 mmol) were added to a flask and the flask evacuated. After refilling with nitrogen, THF (20 mL), diisopropylamine (1 mL) and TMS acetylene (0.35 mL, 2.44 mmol) were added and the resulting mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was partitioned between 25 mL of 1M hydrochloric acid and 25 mL of EtOAc. The aqueous layer was extracted with additional EtOAc and the combined organic layer was dried over MgSO4 and concentrated. The residue was purified flash chromatography (0-100% CH2Cl2/hexanes) to afford 405 mg of the title compound. MS: (+) m/z 381.35 (M+1).

Workup

  1. customthe flask evacuated
  2. additionwere added
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between 25 mL of 1M hydrochloric acid and 25 mL of EtOAc
  5. extractionThe aqueous layer was extracted with additional EtOAc
  6. dry with materialthe combined organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified flash chromatography (0-100% CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-cd7788bfd9b24bcfbf0e82e82ef50d59
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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