3,4,5-Trimethoxybenzaldehyde → HCID 58930491, compound

HRID 252803Notes

Reaction equation

HRID 252803 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[CH:19]=O.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:27][O:26][C:22]1[CH:21]=[C:18]([CH:17]=[C:16]([O:15][CH3:14])[C:23]=1[O:24][CH3:25])[CH2:19][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 12688Dibutyltin dichlorideHCID 12752Phenylsilane2×HCID 21782110methyl 2,3-dihydro-1H-indole-5-carboxylate

Product 1

HCID 58930491HCID 58930491, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 20 (300 mg, 1.69 mmol), 3,4,5-trimethoxybenzaldehyde (365 mg, 1.86 mmol) and dibutyltin dichloride (51 mg, 0.17 mmol) in THF (8 mL) was added phenylsilane (229 μl, 1.86 mmol). The mixture was stirred overnight at room temperature under nitrogen. Additional aldehyde and phenylsilane were added and the stirring continued until starting material was consumed. THF was evaporated in vacuum and the residue was purified by flash chromatography (eluent 20% EtOAc in hexane). The compound was further purified by re-crystallization in a mixture EtOAc/hexane and finally by a second flash chromatography (eluent 20% EtOAc in hexane) to give the title compound 21 (428 mg, 71%) as a white solid. 1H-NMR (DMSO) δ: 2.96 (t, J=8.4 Hz, 2H); 3.45 (t, J=8.7 Hz, 2H); 3.61 (s, 3H); 3.71 (s, 6H); 3.72 (s, 3H); 4.30 (s, 2H); 6.59 (s, 2H); 6.61 (d, J=8.4 Hz, 1H), 7.54 (d, J=1.6 Hz, 1H); 7.63 (dd, J=1.8, 8.4 Hz, 1H).

Workup

  1. customwas consumed
  2. customTHF was evaporated in vacuum
  3. customthe residue was purified by flash chromatography (eluent 20% EtOAc in hexane)
  4. customThe compound was further purified by re-crystallization in a mixture EtOAc/hexane and finally by a second flash chromatography (eluent 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-42bd2cd077b54c73947b34af0983135f
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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