Potassium Acetate → Ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

HRID 1774845Notes

Reaction equation

HRID 1774845 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]([CH3:13])[C:7](=[O:14])[CH2:6][CH2:5]2.Br[C:16]1[C:17]([F:28])=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH3:26])[C:21](=[O:27])[CH2:20][CH2:19]2.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.C([O-])(=O)C.[K+].Br[C:53]1[CH:54]=[C:55]([CH2:59][NH:60][S:61]([CH2:64][CH3:65])(=[O:63])=[O:62])[CH:56]=[N:57][CH:58]=1>C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe].C(Cl)Cl>[F:12][C:11]1[CH:10]=[C:9]2[C:4]([CH2:5][CH2:6][C:7](=[O:14])[N:8]2[CH3:13])=[CH:3][C:2]=1[C:53]1[CH:54]=[C:55]([CH2:59][NH:60][S:61]([CH2:64][CH3:65])(=[O:62])=[O:63])[CH:56]=[N:57][CH:58]=1.[F:28][C:17]1[C:16]([C:53]2[CH:54]=[C:55]([CH2:59][NH:60][S:61]([CH2:64][CH3:65])(=[O:62])=[O:63])[CH:56]=[N:57][CH:58]=2)=[CH:25][CH:24]=[C:23]2[C:18]=1[CH2:19][CH2:20][C:21](=[O:27])[N:22]2[CH3:26]

Participants

8

Reactant 5

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 58215658N-((5-bromopyridin-3-yl)methyl)ethanesulfonamideHCID 866791306-Bromo-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-oneHCID 866791926-bromo-5-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one

Product 2

HCID 86679190Ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amideHCID 86679191Ethanesulfonic acid [5-(5-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

Reagents, catalysts & solvents 1

HCID 178478472(1,1'-Bis(diphenylphosphino)ferrocene)dichloropalladium-dichloromethane (1:1)Catalyst

Procedure

In analogy to the procedure described for the preparation of intermediates A-1 [B], the mixture of 6-bromo-7-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one and 6-bromo-5-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one was reacted with 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) in the presence of potassium acetate and PdCl2(DPPF)-CH2Cl2 and the reaction product was subsequently reacted with ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (intermediate A-11) in analogy to the procedure described for the preparation of example 45. The crude reaction product has been separated by preparative HPLC to give ethanesulfonic acid [5-(7-fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide (example 16) as well as the title compound as a white solid. MS: 378.1 (M+H+)+.

Workup

  1. customIn analogy to the procedure described for the preparation of intermediates A-1 [B]
  2. customdescribed for the preparation of example 45
  3. customThe crude reaction product
  4. customhas been separated by preparative HPLC

Sources & evidence

ORD record
ord-2394b1c880374ed79e6966fc771a73a3
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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