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

HRID 1258238Notes

Reaction equation

HRID 1258238 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].P(Br)(Br)Br.C([O-])(O)=O.[Na+]>CCOCC.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 3

HCID 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 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a 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 Ether: DCM (20 mL; 1:1) was added PBr3 (0.114 mL, 1.21 mol) dropwise at 0° C. The reaction mixture was stirred at RT for 2 h. The reaction mixture was then diluted with DCM and basified with 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, 2 H), 8.24-8.19 (m, 2 H), 8.11-7.94 (m, 3 H), 7.85-7.80 (m, 1 H), 7.59 (d, J=7.2 Hz, 2 H), 7.44 (s, 2 H), 7.21 (d, J=7.2 Hz, 2 H), 5.61 (s, 2 H), 3.38 (s, 2 H), 3.09 (s, 3 H). 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-4010dc7fc415458bb3d8a208726e6945
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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