Styrene → HCID 22494888, compound

HRID 1615275Notes

Reaction equation

HRID 1615275 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.[CH2:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.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>[CH:21](/[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:22]\[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 7501StyreneHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 581896963-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde

Product 1

HCID 22494888HCID 22494888, compoundYield 67%

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 (100 mg, 0.249 mmol), styrene (37 uL, 0.324 mmol), diisopropylethylamine (87 uL, 0.324 mmol) and DMF (2.5 mL) was purged with Ar gas for 20 min at which time Pd(OAc)2 (2.8 mg, 0.0125 mmol) and P(o-tol)3 (11 mg, 0.0374 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 3× with EtOAc 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, 5:1 hexanes/EtOAc) to give the title compound (63 mg, 67%) which was used without further purification. MS ESI 379.2 [M+H]+, calcd for [C22H26N2O2Si+H]+ 379.18.

Workup

  1. additionwere added
  2. temperatureThe reaction was cooled to room temperature
  3. custompartitioned between EtOAc and NH4Cl
  4. extractionThe aqueous layer was extracted 3× with EtOAc
  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, 5:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-62d90061ceab46dcad2f5fb6eb9ac3a2
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…