Acetic Acid → HCID 59556406, compound

HRID 545488Notes

Reaction equation

HRID 545488 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH:15]=O)[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH2:15][NH:24][CH2:23][C:22]3[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57443969Ethyl 6-formylbenzo[b]thiophene-2-carboxylate

Product 1

HCID 59556406HCID 59556406, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 6-formyl-benzo[b]thiophene-2-carboxylic acid ethyl ester (1.05 g, 4.48 mmol) and 4-methoxy-benzylamine (0.76 mL, 5.86 mmol) in anhydrous dichloroethane (40 mL) were added sodium triacetoxyborohydride (2.87 g, 13.5 mmol) and acetic acid (0.25 mL, 4.4 mmol). After the reaction was complete, the reaction mixture was diluted with 60 mL of CH2Cl2 and 40 mL of saturated NaHCO3. The organic layer was separated, washed with 50 mL of water, 50 mL of brine and then dried over Na2SO4. After filtration, the filtrate was concentrated and the residue was purified by flash column chromatography to give 6-[(4-methoxy-benzylamino)-methyl]-benzo[b]thiophene-2-carboxylic acid ethyl ester as a white solid. MS (EI): cal'd 356.1 (MH+), exp 356.1 (MH+).

Workup

  1. customThe organic layer was separated
  2. washwashed with 50 mL of water, 50 mL of brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-d26f35f1de034c09b54ac0996f4c71db
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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