2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → HCID 67372283, compound

HRID 1375375Notes

Reaction equation

HRID 1375375 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[O:4][CH2:3]C1.[CH2:13]([N:17]1[C:21]([CH2:22][NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH3:33])[CH:26]=2)=[C:20]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[NH:19][CH:18]1[I:40])[CH2:14][CH2:15][CH3:16].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(O)(=O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:23]([CH2:22][C:21]3[N:17]([CH2:13][CH2:14][CH2:15][CH3:16])[CH:18]([I:40])[NH:19][C:20]=3[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH3:33])[CH:26]=3)=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

6

Reactant 3

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67371851HCID 67371851, compound

Product 1

HCID 67372283HCID 67372283, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

2,3-Dihydro-benzo[1,4]dioxine-6-carbaldehyde (503 mg) is added to a solution of (1-butyl-2-iodo-4-phenyl-3H-imidazol-5-ylmethyl)-(3-ethoxy-benzyl)-amine (750 mg) in 10 mL of 1,2-dichlorethane followed by the addition of 10 drops of acetyl alcohol. The resulting mixture is stirred at room temperature for 2 hours. 2 Equivalents of NaBH(OAc)3 are added and the stirring is continued overnight. The reaction is quenched with 10 mL water. The organic phase is collected, washed with water and brine, and dried over Na2SO4. Concentration and purification via flash chromatography provides benzo[1,3]dioxol-5-ylmethyl-(1-butyl-2-iodo-4-phenyl-3H-imidazol-5-ylmethyl)-(3-ethoxy-benzyl)-amine (compound 4).

Workup

  1. waitthe stirring is continued overnight
  2. customThe reaction is quenched with 10 mL water
  3. customThe organic phase is collected
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration and purification via flash chromatography

Sources & evidence

ORD record
ord-b80e4ac0143341afb1d46ef3d9050dde
Source dataset
uspto-grants-2007_01
Patent number
US07169775B2

Reaction notes

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