4-Bromo-2-(methylthio)benzo[d]thiazole-6-carbonitrile → (4-Bromo-2-(methylthio)benzo[d]thiazol-6-yl)methanamine

Reaction equation

[Br:1][C:2]1[C:7]2[N:8]=[C:9]([S:11][CH3:12])[S:10][C:6]=2[CH:5]=[C:4]([C:13]#[N:14])[CH:3]=1.FC1C(C#N)=CC2SC(SC)=NC=2C=1>>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([S:11][CH3:12])[S:10][C:6]=2[CH:5]=[C:4]([CH2:13][NH2:14])[CH:3]=1

Participants

Reactant 2

HCID 866811644-Bromo-2-(methylthio)benzo[d]thiazole-6-carbonitrile

HCID 866811685-Fluoro-2-(methylthio)benzo[d]thiazole-6-carbonitrile

Product 1

HCID 86681167(4-Bromo-2-(methylthio)benzo[d]thiazol-6-yl)methanamine

Procedure

(4-Bromo-2-(methylthio)benzo[d]thiazol-6-yl)methanamine was synthesized as a clear oil (794 mg, 79%) using a procedure analogous to that described in Step 3 of Example 154, substituting 4-bromo-2-(methylthio)benzo[d]thiazole-6-carbonitrile from the previous step for 5-fluoro-2-(methylthio)benzo[d]thiazole-6-carbonitrile used in Example 154. LCMS (ESI) m/z 288, 290 (M+H)+.

Sources & evidence

ORD record: ord-c8c7b5621af843428506af42b67c8991
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

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