Methanethiol → 6-Iodo-4-methylsulfanyl-quinoline-3-carbonitrile

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[CH3:15][SH:16].CCN(C(C)C)C(C)C>>[I:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[C:2]2[S:16][CH3:15]

Participants

Reactant 3

HCID 878Methanethiol

HCID 81531Diisopropylethylamine

HCID 224667694-Chloro-6-iodoquinoline-3-carbonitrile

Product 1

HCID 688254066-Iodo-4-methylsulfanyl-quinoline-3-carbonitrile

Procedure

Similar procedure as described in example 39a was used, starting from 4-chloro-6-iodo-quinoline-3-carbonitrile (example 14c), methanethiol and DIEA to give 6-iodo-4-methylsulfanyl-quinoline-3-carbonitrile. LC-MS m/e 327 (MH+).

Sources & evidence

ORD record: ord-7693b44a8f974e38b9fea3eb1f301249
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250515B2

Reaction notes

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