Diethyl Ether → 1-methyl-4-(pyridin-4-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrol-2(5H)-one

HRID 446801Notes

Reaction equation

HRID 446801 reaction equation
O[CH2:2]/[C:3](/[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)=[C:4](/[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)=[CH:11][CH:10]=1)\[C:5]([NH:7][CH3:8])=[O:6].CCOCC.P(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:8][N:7]1[CH2:2][C:3]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:13][CH:14]=2)[C:5]1=[O:6]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 59354792(Z)-4-hydroxy-N-methyl-3-(pyridin-4-yl)-2-(4-(quinolin-2-ylmethoxy)phenyl)but-2-enamide

Product 1

HCID 583680081-methyl-4-(pyridin-4-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrol-2(5H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of (Z)-4-hydroxy-N-methyl-3-(pyridin-4-yl)-2-(4-(quinolin-2-ylmethoxy)phenyl)but-2-enamide (430 mg, 1.01 mmol) in 1:1 ether:DCM (20 mL), PBr3 (0.114 mL, 1.21 mol) was added. The reaction mixture was stirred at RT for 2 h, diluted with DCM and basified with a NaHCO3 solution. The organic layer was separated, washed with water, dried over Na2SO4 and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 1-methyl-4-(pyridin-4-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrol-2(5H)-one (350 mg, 85%) as a solid. 1H NMR (500 MHz, CD3OD): δ 8.81 (d, J=7.8 Hz, 2H), 8.24-8.19 (m, 2H), 8.11-7.94 (m, 3H), 7.85-7.80 (m, 1H), 7.59 (d, J=7.2 Hz, 2H), 7.44 (s, 2H), 7.21 (d, J=7.2 Hz, 2H), 5.61 (s, 2H), 3.38 (s, 2H), 3.09 (s, 3H). MS: M+H: m/z=408.2. HPLC: 89%, (Condition-B).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto obtain the crude product
  6. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-504648e9ea024f93aa7b0ac921f03a9e
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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