Acetic Acid → Methyl 5-ethyl-2-methoxy-6-(6-methyl-5-(pyrrolidin-1-ylmethyl)-6H-thieno[2,3-b]pyrrol-2-yl)nicotinate

HRID 1481713Notes

Reaction equation

HRID 1481713 reaction equation
[CH2:1]([C:3]1[C:4]([C:15]2[S:25][C:18]3[N:19]([CH3:24])[C:20]([CH:22]=O)=[CH:21][C:17]=3[CH:16]=2)=[N:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:2].[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH2:1]([C:3]1[C:4]([C:15]2[S:25][C:18]3[N:19]([CH3:24])[C:20]([CH2:22][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:21][C:17]=3[CH:16]=2)=[N:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 89421794methyl 5-ethyl-6-(5-formyl-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate

Product 1

HCID 71281755Methyl 5-ethyl-2-methoxy-6-(6-methyl-5-(pyrrolidin-1-ylmethyl)-6H-thieno[2,3-b]pyrrol-2-yl)nicotinateYield 86%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To solution of methyl 5-ethyl-6-(5-formyl-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate (49.4 mg, 0.14 mmol) in dichloroethane (1.5 mL) was added pyrrolidine (20 μL, 0.24 mmol) followed by AcOH (15 μL, 0.25 mmol). After stirring at room temperature for 10 min NaBH(OAc)3 (60 mg, 0.28 mmol) was added. Reaction was stirred at room temperature overnight and then quenched with NaHCO3 solution (aqueous saturated, 5 mL). Product was extracted with DCM (3×7 mL). Organic phase was dried over Na2SO4 and solvent was concentrated. Product was purified by column chromatography (MeOH/DCM, 0-5% gradient). Methyl 5-ethyl-2-methoxy-6-(6-methyl-5-(pyrrolidin-1-ylmethyl)-6H-thieno[2,3-b]pyrrol-2-yl)nicotinate (49.7 mg) was obtained in 86% yield. LC-MS 343.1 [M-71+H]+, RT 1.00 min.

Workup

  1. additionwas added
  2. customReaction
  3. customquenched with NaHCO3 solution (aqueous saturated, 5 mL)
  4. extractionProduct was extracted with DCM (3×7 mL)
  5. dry with materialOrganic phase was dried over Na2SO4 and solvent
  6. concentrationwas concentrated
  7. customProduct was purified by column chromatography (MeOH/DCM, 0-5% gradient)

Sources & evidence

ORD record
ord-bb97d8c9625b414cb008c96477dbafe9
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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