Bis(pinacolato)diborane → HCID 86679220, compound

HRID 1774874Notes

Reaction equation

HRID 1774874 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:16]4=[C:17]([CH2:19][CH2:20][CH2:21][N:15]4[C:14](=[O:22])[CH2:13][CH2:12]3)[CH:18]=2)O1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.Br[C:43]1[CH:44]=[C:45]([CH2:49][NH:50][S:51]([CH2:54][CH3:55])(=[O:53])=[O:52])[CH:46]=[N:47][CH:48]=1>>[O:22]=[C:14]1[CH2:13][CH2:12][C:11]2[C:16]3=[C:17]([CH2:19][CH2:20][CH2:21][N:15]13)[CH:18]=[C:9]([C:43]1[CH:44]=[C:45]([CH2:49][NH:50][S:51]([CH2:54][CH3:55])(=[O:52])=[O:53])[CH:46]=[N:47][CH:48]=1)[CH:10]=2

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 58215658N-((5-bromopyridin-3-yl)methyl)ethanesulfonamideHCID 86679221HCID 86679221, compound

Product 1

HCID 86679220HCID 86679220, compound

Procedure

In analogy to the procedure described for the preparation of example 45, 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,6,7-tetrahydropyrido[3,2,1-ij]quinolin-3(5H)-one (prepared from 9-bromo-1,2,6,7-tetrahydropyrido[3,2,1-ij]quinolin-3(51H)-one and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) in analogy to the procedure described for the preparation of intermediate A-1 [B]) has been coupled to ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (intermediate A-11) to give the title compound as an off-white amorphous solid. MS: 386.2 (M+H+).

Workup

  1. customdescribed for the preparation of intermediate A-1 [B])

Sources & evidence

ORD record
ord-a0b6a027e4914acd9d0dc0f61f1021f6
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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