1-(3-Bromo-5-chloro-pyridin-4-yl)-ethanol → 1-[3-Chloro-5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-4-yl]-ethanol

HRID 712695Notes

Reaction equation

HRID 712695 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:11])[C:7]=1[CH:8]([OH:10])[CH3:9].CC1(C)C(C)(C)OB([C:20]2[CH:21]=[C:22]3[C:27](=[N:28][CH:29]=2)[NH:26][CH2:25][CH2:24][CH2:23]3)O1>>[Cl:11][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:24]2[CH:25]=[N:26][C:27]3[NH:28][CH2:29][CH2:20][CH2:21][C:22]=3[CH:23]=2)[C:7]=1[CH:8]([OH:10])[CH3:9]

Participants

3

Reactant 2

HCID 671550211-(3-Bromo-5-chloro-pyridin-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 1176671651-[3-Chloro-5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-4-yl]-ethanol

Procedure

1-[3-Chloro-5-(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-5-chloro-pyridin-4-yl)-ethanol (which is prepared according to Step 1 of Example 78) and crude 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine (that is prepared according to Step 4 of Example 105).

Sources & evidence

ORD record
ord-f89eab1dfed046478776f80b4ebfc44d
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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