p-Toluenesulfonic acid → 3-(7-Methoxy-indol-1-yl)-3-pyridin-3-yl-propan-1-ol

HRID 250209Notes

Reaction equation

HRID 250209 reaction equation
C[O:2][C:3](=O)[CH:4]([CH:12]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[O:28][CH3:29])[CH:21]=[CH:20]1)[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)C(OC(C)(C)C)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:29][O:28][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[N:19]([CH:12]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:4][CH2:3][OH:2])[CH:20]=[CH:21]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 580884582-[(7-Methoxy-indol-1-yl)-pyridin-3-yl-methyl]-malonic acid tert-butyl ester methyl ester

Product 1

HCID 580884743-(7-Methoxy-indol-1-yl)-3-pyridin-3-yl-propan-1-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[(7-Methoxy-indol-1-yl)-pyridin-3-yl-methyl]-malonic acid tert-butyl ester methyl ester (0.200 g) was dissolved in toluene (50 ml) and treated with p-toluenesulfonic acid (0.102 g). The mixture was brought to reflux temperature and stirred for 4 hours. The reaction mixture was partitioned between ethyl acetate and aqueous bicarbonate solution, the organic layer was dried over magnesium sulfate, filtered and evaporated to dryness to afford 3-(7-methoxy-indol-1-yl)-3-pyridin-3-yl-propan-1-ol as an oil which was purified by column chromatography (ethyl acetate-hexane 3:7).

Workup

  1. temperatureto reflux temperature
  2. customThe reaction mixture was partitioned between ethyl acetate and aqueous bicarbonate solution
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-767215e18a4249a081b3ba6640166170
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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