3,4,5-Trimethoxybenzaldehyde → HCID 59699782, compound

HRID 2234555Notes

Reaction equation

HRID 2234555 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])=[CH:14][N:13](S(C3C=CC(C)=CC=3)(=O)=O)[C:10]2=[N:11][CH:12]=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([CH:41]=[C:42]([O:46][CH3:47])[C:43]=1[O:44][CH3:45])[CH:39]=[O:40]>C1COCC1>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([CH:39]([C:38]3[CH:41]=[C:42]([O:46][CH3:47])[C:43]([O:44][CH3:45])=[C:36]([O:35][CH3:34])[CH:37]=3)[OH:40])[CH:8]=2)[NH:13][CH:14]=1

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 59699754HCID 59699754, compoundHCID 178418339Butyllithium

Product 1

HCID 59699782HCID 59699782, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution 1.5M n-BuLi in hexanes (160 μL, 0.24 mmol) was added to a solution of the 5-bromo-3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (91.5 mg, 0.20 mmol) in 2 ml THF at −78° C. The mixture was stirred at −78° C. for 30 minutes before 3,4,5-trimethoxy-benzaldehyde (94.2 mg, 0.48 mmol) in 3 mL of THF was added. The mixture was stirred at −78° C. for 1 hour and then at 0° C. for 30 minutes, quenched with MeOH, and then concentrated. The crude residue was purified by silica gel chromatography using a gradient of ethyl acetate in hexanes to give [3-(2-Methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-(3,4,5-trimethoxy-phenyl)-methanol (32 mg, 38% yield) as a white solid. MS: m/z 420.1 [MH+].

Workup

  1. additionwas added
  2. waitat 0° C. for 30 minutes
  3. customquenched with MeOH
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8237bc1e9ddb4a7fa14a27364f234ba0
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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