Butanethiol → 4-Butylsulfanyl-6-iodo-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].[CH2:15]([SH:19])[CH2:16][CH2:17][CH3:18].CCN(C(C)C)C(C)C>>[CH2:15]([S:19][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])[CH2:16][CH2:17][CH3:18]

Participants

Reactant 3

HCID 8012Butanethiol

HCID 81531Diisopropylethylamine

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

Product 1

HCID 688248274-Butylsulfanyl-6-iodo-quinoline-3-carbonitrile

Procedure

Similar procedure as described in example 39a was used, starting from 4-chloro-6-iodo-quinoline-3-carbonitrile (example 14c), butane-1-thiol and DIEA to give 4-butylsulfanyl-6-iodo-quinoline-3-carbonitrile. LC-MS m/e 369 (MH+).

Sources & evidence

ORD record: ord-8e7a93dd9db9497590c7c9fc8018bad0
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250515B2

Reaction notes

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