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

HRID 1765578Notes

Reaction equation

HRID 1765578 reaction equation
IC1N(S(C2C=CC(C)=CC=2)(=O)=O)C2N=CC=C(C#N)C=2C=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=[C:28]2[C:34]1[N:44](S(C2C=CC(C)=CC=2)(=O)=O)[C:37]2[N:38]=[CH:39][CH:40]=[C:41]([C:42]#[N:43])[C:36]=2[CH:35]=1>C(OCC)(=O)C.CCCCCCC>[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=[C:28]2[C:34]1[NH:44][C:37]2[N:38]=[CH:39][CH:40]=[C:41]([C:42]#[N:43])[C:36]=2[CH:35]=1

Participants

4

Reactant 2

HCID 224772152-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrileHCID 224773222-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Product 1

HCID 224772482-(5-Methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

By proceeding in a similar manner to Reference Example 12(a) but using 2-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile [Reference Example 62(a)] there was prepared the title compound as a yellow solid, m.p. 303–304° C., TLC RF=0.07 (ethyl acetate/heptane 1:1) and 2-(5-methoxy-1H-indol-3-y)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile [Reference Example 100] as a brown oil. MS: 443 (MH+). TLC: RF=0.38 (ethyl acetate/heptane 1:1).

Sources & evidence

ORD record
ord-ba5cdb8dfcaf41f68bc62f7bb27f2626
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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