2-(5-Bromo-pyridin-3-yl)-2-methyl-propionic acid benzyl ester → 6-[5-(1-Benzyloxycarbonyl-1-methyl-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

HRID 712715Notes

Reaction equation

HRID 712715 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[C:10]([C:13]1[CH:14]=[N:15][CH:16]=[C:17](Br)[CH:18]=1)([CH3:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][C:26]([N:28]1[C:37]2[C:32](=[CH:33][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:35][N:36]=2)[CH2:31][CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26]([N:28]1[C:37]2[C:32](=[CH:33][C:34]([C:17]3[CH:16]=[N:15][CH:14]=[C:13]([C:10]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:20])([CH3:12])[CH3:11])[CH:18]=3)=[CH:35][N:36]=2)[CH2:31][CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 1176676812-(5-Bromo-pyridin-3-yl)-2-methyl-propionic acid benzyl esterHCID 1232163436-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 1176673576-[5-(1-Benzyloxycarbonyl-1-methyl-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Procedure

6-[5-(1-Benzyloxycarbonyl-1-methyl-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester is synthesized according to the procedure of Suzuki Coupling Method VI using 2-(5-bromo-pyridin-3-yl)-2-methyl-propionic acid benzyl ester and crude 6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (Intermediate G).

Sources & evidence

ORD record
ord-0e9a216bdf2249be8a68e5b06db44190
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…