1-Methylpiperazine → 7-(2-Fluoro-4-nitrophenoxy)-2-(5-((4-methylpiperazin-1-yl)methyl)pyridin-2-yl)thieno[3,2-b]pyridine

HRID 1711112Notes

Reaction equation

HRID 1711112 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][N:15]=3)[S:13][C:6]=12.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:21]=[CH:20][C:17]([CH2:18][N:33]4[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]4)=[CH:16][N:15]=3)[S:13][C:6]=12

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 594576666-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)nicotinaldehyde

Product 1

HCID 594577107-(2-Fluoro-4-nitrophenoxy)-2-(5-((4-methylpiperazin-1-yl)methyl)pyridin-2-yl)thieno[3,2-b]pyridineYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 438 (451 mg, 1.14 mmol) and 1-methylpiperazine (152 μL, 137 mg, 1. 37 mmol) in DCM (7 mL) was stirred at room temperature for 10 min. It was then treated with NaBH(OAc)3 (340 mg, 1.60 mmol) and stirred at room temperature overnight. The reaction mixture was the diluted with DCM (20 mL) and washed with saturated NaHCO3 solution (20 mL). It was then dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash chromatography using the gradient 30-50% MeOH (with 2% Et3N) in EtOAc as an eluent, yielding 439 of (308 mg, 52% yield). LCMS: (M+H) 480.0 (100%).

Workup

  1. stirringstirred at room temperature overnight
  2. washwashed with saturated NaHCO3 solution (20 mL)
  3. dry with materialIt was then dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-61414783f7a84396805d69db6237f878
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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