N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide → HCID 86696557, compound

HRID 1854839Notes

Reaction equation

HRID 1854839 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]2=[O:20].CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][C:32]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[CH:31][CH:30]=2)O1>>[CH:13]1([C:9]2[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6](=[O:20])[N:5]3[C:10]=2[C:11]([CH3:12])=[C:2]([C:29]2[CH:30]=[CH:31][C:32]([NH:35][S:36]([CH3:39])(=[O:37])=[O:38])=[CH:33][CH:34]=2)[CH:3]=[CH:4]3)[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 16217653N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamideHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696557HCID 86696557, compoundYield 77.8%

Procedure

Methyl 1-cyclopropyl-9-methyl-8-(4-(methylsulfonamido)-phenyl)-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A using methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (74 mg, 0.25 mmol) and N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-methane-sulfonamide (96 mg, 0.32 mmol). Compound precipitated from solution and was filtered off and dried in vacuo to afford the title compound as a yellow solid (83 mg, 77%). ESI-MS m/z: 427 (M+H)+.

Workup

  1. customMethyl 1-cyclopropyl-9-methyl-8-(4-(methylsulfonamido)-phenyl)-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. customCompound precipitated from solution
  3. filtrationwas filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6893891f79d34306a17f10faaaf567fe
Source dataset
uspto-grants-2015_02
Patent number
US08962842B2

Reaction notes

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