6-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-azatricyclo[6.3.1.0,4,12]dodeca-4(12),5,7-trien-11-one → Ethanesulfonic acid [5-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-pyridin-3-ylmethyl]-amide

HRID 1774873Notes

Reaction equation

HRID 1774873 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][N:15]4[C:14](=[O:21])[CH2:13][CH2:12]3)[CH:18]=2)O1.Br[C:24]1[CH:25]=[C:26]([CH2:30][NH:31][S:32]([CH2:35][CH3:36])(=[O:34])=[O:33])[CH:27]=[N:28][CH:29]=1>>[O:21]=[C:14]1[CH2:13][CH2:12][C:11]2[C:16]3=[C:17]([CH2:19][CH2:20][N:15]13)[CH:18]=[C:9]([C:24]1[CH:25]=[C:26]([CH2:30][NH:31][S:32]([CH2:35][CH3:36])(=[O:33])=[O:34])[CH:27]=[N:28][CH:29]=1)[CH:10]=2

Participants

3

Reactant 2

HCID 529370426-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-azatricyclo[6.3.1.0,4,12]dodeca-4(12),5,7-trien-11-oneHCID 58215658N-((5-bromopyridin-3-yl)methyl)ethanesulfonamide

Product 1

HCID 86679219Ethanesulfonic acid [5-(4-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-pyridin-3-ylmethyl]-amide

Procedure

In analogy to the procedure described for the preparation of example 45, 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-4(2H)-one has been coupled to ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (intermediate A-11) to give the title compound as a colorless amorphous solid. MS: 372.2 (M+H+).

Sources & evidence

ORD record
ord-ba8ed63684ac4b3fa13831f1b6e9ea5e
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

Loading…