Acetic Acid → 5-Fluoro-8-{4-[4-(5-fluoro-1-benzofuran-3-yl)-1-piperazinyl]-1-piperidinyl}quinoline

HRID 2241974Notes

Reaction equation

HRID 2241974 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[F:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][CH:26]=[C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[C:24]=2[CH:34]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([N:31]3[CH2:32][CH2:33][N:28]([C:25]4[C:24]5[CH:34]=[C:20]([F:19])[CH:21]=[CH:22][C:23]=5[O:27][CH:26]=4)[CH2:29][CH2:30]3)[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 214718555-Fluoro-3-piperazino benzofuranHCID 592048481-(5-Fluoroquinolin-8-yl)piperidin-4-one

Product 1

HCID 120043105-Fluoro-8-{4-[4-(5-fluoro-1-benzofuran-3-yl)-1-piperazinyl]-1-piperidinyl}quinolineYield 27.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.200 g of 1-(5-fluoro-quinolin-8-yl)-piperidin-4-one (Example C, Step 3, 0.20 g) and 5-fluoro-3-piperazino benzofuran (Step 2, 0.20 g) in CH2Cl2 (10 mL) was added sodium triacetoxyborohydride (0.224 g) and 0.02 mL acetic acid. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH, and the product was extracted with CH2Cl2. The organic phase was washed with water and dried over magnesium sulfate. The product was filtered through 100 ML of silica gel using 50% Ethyl acetate/Hexanes then 100% Ethyl acetate to give 0.100 g of the desired product. Mp: 187-189° C.; MS (ES) m/z (relative intensity): 449 (M++−H, 100).

Workup

  1. customIt was quenched with 1N NaOH
  2. extractionthe product was extracted with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe product was filtered through 100 ML of silica gel using 50% Ethyl acetate/Hexanes

Sources & evidence

ORD record
ord-3efa7a0a809447ddaa80255df082a90c
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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