4-Amino-2-bromopyridine → 1-(5-(4-Aminopyridin-2-yl)pyrimidin-2-yl)-N,N-dimethyl-3-(methylsulfinyl)-1H-indole-6-carboxamide

HRID 630519Notes

Reaction equation

HRID 630519 reaction equation
BrC1C=NC(N2C3C(=CC=C(C(N(C)C)=O)C=3)C(SC)=C2)=NC=1.Br[C:25]1[CH:30]=[C:29]([NH2:31])[CH:28]=[CH:27][N:26]=1.CC1C=CN=C(C2C=NC(N3C4C(=CC=C(C(OC)=O)C=4)C(SC)=C3)=NC=2)C=1.CC1C=CN=C([C:67]2[CH:68]=[N:69][C:70]([N:73]3[C:81]4[C:76](=[CH:77][CH:78]=[C:79]([C:82]([N:84]5[CH2:88]CC[CH2:85]5)=[O:83])[CH:80]=4)[C:75]([S:89]([CH3:91])=[O:90])=[CH:74]3)=[N:71][CH:72]=2)C=1>>[NH2:31][C:29]1[CH:28]=[CH:27][N:26]=[C:25]([C:67]2[CH:72]=[N:71][C:70]([N:73]3[C:81]4[C:76](=[CH:77][CH:78]=[C:79]([C:82]([N:84]([CH3:85])[CH3:88])=[O:83])[CH:80]=4)[C:75]([S:89]([CH3:91])=[O:90])=[CH:74]3)=[N:69][CH:68]=2)[CH:30]=1

Participants

5

Reactant 4

HCID 3464554-Amino-2-bromopyridineHCID 1186662781-(5-Bromopyrimidin-2-yl)-N,N-dimethyl-3-(methylthio)-1H-indole-6-carboxamideHCID 118671669(1-(5-(4-Methylpyridin-2-yl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(pyrrolidin-1-yl)methanoneHCID 118676909Methyl 1-(5-(4-methylpyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate

Product 1

HCID 1186663901-(5-(4-Aminopyridin-2-yl)pyrimidin-2-yl)-N,N-dimethyl-3-(methylsulfinyl)-1H-indole-6-carboxamide

Procedure

1-(5-Bromopyrimidin-2-yl)-N,N-dimethyl-3-(methylthio)-1H-indole-6-carboxamide was converted into a boronic ester that was reacted in a Suzuki reaction with 2-bromopyridin-4-amine and the resulting product was then oxidized towards the sulfoxide (analogously to the protocols 269a) and 269d), respectively). White solid. Yield: 0.095 g

Sources & evidence

ORD record
ord-1ee814e879e54f20aef6a99cb087f6ae
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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