Methyl iodide → 1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 490492Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:9](C3C4C(=CC(OCC5C=CC=CC=5)=C(OC)C=4)NC=3)=[CH:10][C:3]=12.CI>>[C:36]1([CH3:39])[CH:35]=[CH:34][C:33]([S:30]([N:8]2[C:4]3=[N:5][CH:6]=[CH:7][CH:2]=[C:3]3[CH:10]=[CH:9]2)(=[O:32])=[O:31])=[CH:38][CH:37]=1

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 67147592HCID 67147592, compound

Product 1

HCID 14799661-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Procedure

4-Chloro-2-[1-methyl-5-methoxy-6-benzyloxy)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine is prepared by following the procedure described in example 89c, but using 2.5 g of 4-chloro-2-(5-methoxy-6-benzyloxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 0.335 ml of methyl iodide. After purification by flash chromatography (silica, 40/60 by volume ethyl acetate/cyclohexane as eluents, argon), 2.1 g of 4-chloro-2-(1-methyl-5-methoxy-6-benzyloxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine are obtained, the characteristics of which are as follows:

Workup

customAfter purification by flash chromatography (silica, 40/60 by volume ethyl acetate/cyclohexane as eluents, argon), 2.1 g of 4-chloro-2-(1-methyl-5-methoxy-6-benzyloxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine
customare obtained

Sources & evidence

ORD record: ord-bb3d6b7d0ad14872b0db65d93feeb95d
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

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