Styrylboronic acid → HCID 58382485, compound

HRID 1627985Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]([CH2:11][CH3:12])=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([CH3:24])[O:23][CH2:22][CH2:21][O:20]4)=[CH:15][CH:14]=3)[N:8]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:5]2=[N:6][CH:7]=1.[CH:33](/B(O)O)=[CH:34]\[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH2:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2](/[CH:33]=[CH:34]/[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:3]=2)[N:8]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:9]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([CH3:24])[O:23][CH2:22][CH2:21][O:20]2)=[CH:15][CH:14]=1)[CH3:12]

Participants

Reactant 2

HCID 5702628Styrylboronic acid

HCID 58381973HCID 58381973, compound

Product 1

HCID 58382485HCID 58382485, compound

Procedure

The precursor to Example #W.1,8-ethyl-1-methyl-7-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine, was prepared as shown in Scheme B. 2-Bromo-7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (Preparation #5) and (E)-styreneboronic acid are reacted following conditions given in D to give (E)-7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-2-styryl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine. This alkene is then cleaved following the conditions given in E to give an aldehyde, reduced using conditions described in F to give an alcohol, converted to an azide following G, and then reduced following conditions given in I to give (7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine. The amine is then coupled with Ac2O following conditions described in J.2 and then cyclized using the conditions described in L.1 with mercury(II) trifluoroacetate as the mercury salt to give the precursor to Example #W.1. The reaction sequence detailed above is translated in the preparations and examples section to “prepared using D from Preparation #5 with (E)-styreneboronic acid, E, F, G, I, J.2 with Ac2O and L.1 with mercury(II) trifluoracetate.”

Sources & evidence

ORD record: ord-5fcf4ec58b134a65a9e0789310926fc4
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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