5-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine → 4-(2-(4-(7-(1H-indol-5-yl)-5H-pyrrolo[3,2-b]pyrazin-2-yl)-2-methoxyphenoxy)ethyl)morpholine

HRID 333155Notes

Reaction equation

HRID 333155 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[CH:14][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12]N[CH2:10][CH2:9]1.Br[C:28]1[N:33]=[C:32]2[C:34]([C:47]3[CH:48]=[C:49]4[C:53](=[CH:54][CH:55]=3)[NH:52][CH:51]=[CH:50]4)=[CH:35][N:36](S(C3C=CC(C)=CC=3)(=O)=O)[C:31]2=[N:30][CH:29]=1.BrC1C=C2C(C3C=C4C(=CC=3)NC=C4)=CN(S(C3C=CC(C)=CC=3)(=O)=[O:76])C2=NC=1>>[NH:52]1[C:53]2[C:49](=[CH:48][C:47]([C:34]3[C:32]4=[N:33][C:28]([C:16]5[CH:15]=[CH:14][C:4]([O:5][CH2:6][CH2:7][N:8]6[CH2:9][CH2:10][O:76][CH2:12][CH2:13]6)=[C:3]([O:2][CH3:1])[CH:17]=5)=[CH:29][N:30]=[C:31]4[NH:36][CH:35]=3)=[CH:55][CH:54]=2)[CH:50]=[CH:51]1

Participants

4

Reactant 3

HCID 667791765-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 667799091-(2-(2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)piperazineHCID 866626782-bromo-7-(1H-indol-5-yl)-5-tosyl-5H-pyrrolo[3,2-b]pyrazine

Product 1

HCID 462345104-(2-(4-(7-(1H-indol-5-yl)-5H-pyrrolo[3,2-b]pyrazin-2-yl)-2-methoxyphenoxy)ethyl)morpholine

Procedure

Compound AZ was prepared by a method analogous to that described in Example 36 by substituting 4-(2-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)morpholine for 1-(2-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)piperazine and 2-bromo-7-(1H-indol-5-yl)-5-tosyl-5H-pyrrolo[3,2-b]pyrazine for intermediate B. HPLC retention time: 1.59 minutes. MS ESI (m/z): 470.4 (M+H)+, calc. 469.

Workup

  1. customCompound AZ was prepared by a method analogous to

Sources & evidence

ORD record
ord-09252101eee34466af517e021e148cdc
Source dataset
uspto-grants-2014_11
Patent number
US08877772B2

Reaction notes

Loading…