HCID 1448020, compound → HCID 69844560, compound

HRID 1368964Notes

Reaction equation

HRID 1368964 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][C:9]2[S:11][C:12]([CH:14]=O)=[CH:13][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[BH3-]C#N.[Na+]>ClC(Cl)C>[CH2:1]([O:3][C:4]([C:6]1[NH:10][C:9]2[S:11][C:12]([CH3:14])=[CH:13][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 1448020HCID 1448020, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 69844560HCID 69844560, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Using a procedure by C. K. Lau et. al. (J. Org. Chem., 51: 3038-3043 (1986)), a mixture of 2-formyl-6H-thieno[2,3-b]pyrrole-5-carboxylic acid ethyl ester (Soth, S. et al., Bull. Soc. Chim. Fr., 2511-2515 (1975); 500 mg, 2.24 mmol), Znl2(1.08 g, 3.36 mmol), and NaBH3CN (1.06 g, 16.8 mmol) in dichloroethane (25 mL) was stirred for 7 d and quenched with saturated aqueous NH4Cl (25 mL). The resultant biphasic mixture was stirred for an additional 30 min, extracted with ethyl acetate, dried over Na2SO4, and concentrated. The product was purified by Chromatotron-chromatography (3:2 hexanes:ether) and obtained as a white foam (233 mg, 50%).

Workup

  1. customquenched with saturated aqueous NH4Cl (25 mL)
  2. stirringThe resultant biphasic mixture was stirred for an additional 30 min
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe product was purified by Chromatotron-chromatography (3:2 hexanes:ether)

Sources & evidence

ORD record
ord-ea7b3a2065014ad7b1d81e2c18c64f80
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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