3,5-Dibromopyridine → HCID 86679215, compound

HRID 1774870Notes

Reaction equation

HRID 1774870 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH2:12][CH2:11]3)[CH:5]=[N:6][CH:7]=1.CN1C2C(=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)CCC1=O.BrC1C=NC=C(Br)C=1.[C:49]([O:53][C:54]([N:56]1[CH:61]=[C:60](B2OC(C)(C)C(C)(C)O2)[CH2:59][CH2:58][CH2:57]1)=[O:55])([CH3:52])([CH3:51])[CH3:50]>>[C:49]([O:53][C:54]([N:56]1[CH2:61][CH2:60][CH2:59][C:58]([C:2]2[CH:7]=[N:6][CH:5]=[C:4]([C:8]3[CH:9]=[C:10]4[C:15](=[CH:16][CH:17]=3)[N:14]([CH3:18])[C:13](=[O:19])[CH2:12][CH2:11]4)[CH:3]=2)=[CH:57]1)=[O:55])([CH3:52])([CH3:50])[CH3:51]

Participants

5

Reactant 4

HCID 693693,5-DibromopyridineHCID 59327225tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylateHCID 722082331-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 86679216HCID 86679216, compound

Product 1

HCID 86679215HCID 86679215, compound

Procedure

In analogy to the procedure described for the preparation of example 45, 6-(5-bromo-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one (prepared from 1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-1) and 3,5-dibromo pyridine also with a procedure as used for the preparation of example 45) has been coupled to 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester to give the title compound as an amorphous colorless solid. MS: 420.5 (M+H+).

Workup

  1. customas used for the preparation of example 45)

Sources & evidence

ORD record
ord-94be94e18d0c4557b6ee75f295b54015
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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