1-(3-Bromopyridin-4-yl)ethanol → 1-[3-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-4-yl]-ethanol

HRID 712702Notes

Reaction equation

HRID 712702 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([OH:10])[CH3:9].CC1(C)C(C)(C)OB([C:19]2[CH:20]=[C:21]3[C:26](=[N:27][CH:28]=2)[NH:25][CH2:24][CH2:23][CH2:22]3)O1>>[N:25]1[C:26]2[NH:27][CH2:28][CH2:19][CH2:20][C:21]=2[CH:22]=[C:23]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[CH:8]([OH:10])[CH3:9])[CH:24]=1

Participants

3

Reactant 2

HCID 667978531-(3-Bromopyridin-4-yl)ethanolHCID 1189899286-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-1,8-naphthyridine

Product 1

HCID 1176670831-[3-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-4-yl]-ethanol

Procedure

1-[3-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-4-yl]-ethanol is synthesized according to the procedure of Suzuki Coupling Method VI using 1-(3-bromo-pyridin-4-yl)-ethanol and crude 6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine (which is prepared according to Step 4 of Example 105).

Sources & evidence

ORD record
ord-99878417b3c94a48aac2edf7c222325d
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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