1-Methoxy-2-propanol → 2-[5-(2-Methoxy-1-methyl-ethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1765600Notes

Reaction equation

HRID 1765600 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC([N+](C(OC(C)C)=O)=[N-])=O)(C)C.[CH3:34][N:35]1[C:43]2[C:38](=[CH:39][C:40]([OH:44])=[CH:41][CH:42]=2)[C:37]([C:45]2[N:53]([S:54]([C:57]3[CH:62]=[CH:61][C:60]([CH3:63])=[CH:59][CH:58]=3)(=[O:56])=[O:55])[C:48]3=[N:49][CH:50]=[CH:51][CH:52]=[C:47]3[CH:46]=2)=[CH:36]1.[CH3:64][O:65][CH2:66][CH:67](O)[CH3:68]>C1(C)C=CC=CC=1>[CH3:64][O:65][CH2:66][CH:67]([CH3:68])[O:44][C:40]1[CH:39]=[C:38]2[C:43](=[CH:42][CH:41]=1)[N:35]([CH3:34])[CH:36]=[C:37]2[C:45]1[N:53]([S:54]([C:57]2[CH:62]=[CH:61][C:60]([CH3:63])=[CH:59][CH:58]=2)(=[O:56])=[O:55])[C:48]2=[N:49][CH:50]=[CH:51][CH:52]=[C:47]2[CH:46]=1

Participants

6

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 11776TriphenylphosphineHCID 22145704Diisopropyl diazodicarboxylateHCID 224772511-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-ol

Product 1

HCID 224772702-[5-(2-Methoxy-1-methyl-ethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of triphenylphosphine (470 mg) and diisopropyldiazodicarboxylate (350 μl) in dry toluene (15 mL) was treated with 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-ol [150 mg, Reference Example 14(a)] followed by 1-methoxy-2-propanol (150 μl). The resulting mixture was heated under reflux for 5 hours then cooled and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1, v/v) to give the title compound (50 mg) as a clear oil. TLC: RF=0.65 (pentane/ethyl acetate: 1/1). MS: 480(MH+).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperaturethen cooled
  4. customevaporated
  5. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1

Sources & evidence

ORD record
ord-dfcf8c9222df4474b029f3834ab7b57c
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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