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

HRID 1774875Notes

Reaction equation

HRID 1774875 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][C:32](=[O:40])[C:33]2[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][N:34]=2)[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][C:32]([C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][N:34]=3)=[O:40])[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 86679147N-((5-Bromopyridin-3-yl)methyl)-3-chloropicolinamide

Product 1

HCID 866792223-Chloro-pyridine-2-carboxylic 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 N-((5-bromopyridin-3-yl)methyl)-3-chloropicolinamide (intermediate A-56) to give the title compound as off-white solid. MS: 419.3 (M+H+).

Sources & evidence

ORD record
ord-e46eede24be24c54aa1ff1ebeee7cb01
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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