4'-Methoxy-(1,1'-biphenyl)-4-carboxaldehyde → N1-(5-bromobenzo[d]isothiazol-3-yl)-N3-((4'-methoxybiphenyl-4-yl)methyl)propane-1,3-diamine

HRID 502565Notes

Reaction equation

HRID 502565 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])[C:6]=2[CH:15]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:30][C:27]3[CH:26]=[CH:25][C:24]([C:21]4[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=4)=[CH:29][CH:28]=3)[C:6]=2[CH:15]=1

Participants

7

Reactant 3

HCID 13944874'-Methoxy-(1,1'-biphenyl)-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58726901N1-(5-bromobenzo[d]isothiazol-3-yl)propane-1,3-diamine

Product 1

HCID 58727092N1-(5-bromobenzo[d]isothiazol-3-yl)-N3-((4'-methoxybiphenyl-4-yl)methyl)propane-1,3-diamineYield 40.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N1-(5-Bromobenzo[d]isothiazol-3-yl)propane-1,3-diamine (190 mg, 0.66 mmol) and 4′-methoxybiphenyl-4-carbaldehyde (140 mg, 0.66 mmol) were combined in 1,2-dichloroethane (30 mL) and treated with sodium triacetoxyborohydride (280 mg, 1.32 mmol) and acetic acid (one drop). The mixture was sonicated at room temperature for 18 h. The reaction was diluted with ethyl acetate and then washed with water, brine and saturated sodium bicarbonate solution. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography, on silica gel, eluting with 98:2 methylene chloride:methanol to yield N1-(5-bromobenzo[d]isothiazol-3-yl)-N3-((4′-methoxybiphenyl-4-yl)methyl)propane-1,3-diamine (130 mg) as a yellow solid. MW=482 confirmed by LC-MS, tr=3.24 min (Method B) MH+=481-483.

Workup

  1. customThe mixture was sonicated at room temperature for 18 h
  2. washwashed with water, brine and saturated sodium bicarbonate solution
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by flash column chromatography, on silica gel
  7. washeluting with 98:2 methylene chloride

Sources & evidence

ORD record
ord-2130aeb10882463fb20b6986130f3586
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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