4-Vinylpyridine → HCID 86651957, compound

HRID 1615272Notes

Reaction equation

HRID 1615272 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=1.[CH:21]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)=[CH2:22].C(N(C(C)C)CC)(C)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[N:26]1[CH:27]=[CH:28][C:23](/[CH:21]=[CH:22]/[C:2]2[C:10]3[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=3)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=2)=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 75024-VinylpyridineHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 581896963-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde

Product 1

HCID 86651957HCID 86651957, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (2.0 g, 4.98 mmol), 4-vinylpyridine (0.69 mL, 6.47 mmol), diisopropylethylamine (1.74 mL, 9.96 mmol) and DMF (50 mL) was purged with Ar gas for 20 min at which time Pd(OAc)2 (112 mg, 0.500 mmol) and P(o-tol)3 (457 mg, 1.50 mmol) were added and the reaction heated to 100° C. for 20 hours. The reaction was cooled to room temperature and partitioned between EtOAc and NH4Cl. The aqueous layer was extracted with EtOAc (3×) and the combined organics washed with water (2×) and brine (2×). The organic layer was dried over MgSO4 and the EtOAc removed in vacuo. The residue was purified by column chromatography (silica gel, 97:3 CH2Cl2/MeOH) to give 927 mg, 49% of the title compound which was used without further purification. MS ESI 380.2 [M+H]+, calcd for [C21H25N3O2Si+H]+ 380.18.

Workup

  1. additionwere added
  2. temperatureThe reaction was cooled to room temperature
  3. custompartitioned between EtOAc and NH4Cl
  4. extractionThe aqueous layer was extracted with EtOAc (3×)
  5. washthe combined organics washed with water (2×) and brine (2×)
  6. dry with materialThe organic layer was dried over MgSO4
  7. customthe EtOAc removed in vacuo
  8. customThe residue was purified by column chromatography (silica gel, 97:3 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-68ea1e4f5bee4124b912a31c264fc471
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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