HCID 1448020, compound → HCID 69844560, compound

HRID 2306794Notes

Reaction equation

HRID 2306794 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.[Zn+2].[I-].[I-]>[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

5

Reactant 2

HCID 1448020HCID 1448020, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 69844560HCID 69844560, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 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), ZnI2 (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-d84b87f70ca440ab897f73f4cb790c55
Source dataset
uspto-grants-2004_12
Patent number
US06828343B2

Reaction notes

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