HCID 117667373, compound → HCID 117667659, compound

HRID 712776Notes

Reaction equation

HRID 712776 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[C:12]#[N:13])[N:8]([C:14]([NH2:16])=[O:15])[CH2:7][CH2:6][CH2:5]2.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]([C:31]3([OH:37])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:28]=[N:29][CH:30]=2)O1>>[C:12]([C:11]1[N:10]=[C:9]2[C:4]([CH2:5][CH2:6][CH2:7][N:8]2[C:14]([NH2:16])=[O:15])=[CH:3][C:2]=1[C:25]1[CH:30]=[N:29][CH:28]=[C:27]([C:31]2([OH:37])[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)[CH:26]=1)#[N:13]

Participants

3

Reactant 2

HCID 117667373HCID 117667373, compoundHCID 123231095HCID 123231095, compound

Product 1

HCID 117667659HCID 117667659, compound

Procedure

6-Bromo-7-cyano-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide is coupled with 4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-tetrahydro-pyran-4-ol (which is prepared according to Step 4 of Example 119) to give the titled product using Suzuki Coupling Method VI.

Sources & evidence

ORD record
ord-164db7a138964923864a33daab176f78
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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