Dimethylformamide → HCID 86671499, compound

HRID 536626Notes

Reaction equation

HRID 536626 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[Br:13][C:14]1[C:15]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)=[CH:16][S:17][CH:18]=1.CN([CH:30]=[O:31])C>C1COCC1>[Br:13][C:14]1[C:15]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)=[CH:16][S:17][C:18]=1[CH:30]=[O:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 67256473HCID 67256473, compound2×HCID 178418339Butyllithium

Product 1

HCID 86671499HCID 86671499, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of diisopropylamine (1.2 g, 11.4 mmol) in 20 mL of anhydrous THF was added n-BuLi (3.7 mL, 2.5 M in hexane) at −78° C. After the mixture was stirred at this temperature for 0.5 h, a solution of 4-(4-bromothiophen-3-yl)benzonitrile (prepared in Step 1 of Compound 2) (2.0 g, 7.6 mmol) in anhydrous THF (20 mL) was added dropwise. The mixture was stirred at −78° C. for 15 min., a solution of DMF (611 mg, 8.4 mmol) in THF (5 mL) was added. The reaction mixture was stirred at −78° C. for 0.5 h, and at room temperature for 2 h. The mixture was quenched with saturated NH4Cl aqueous solution, extracted with EtOAc, concentrated, and purified by column chromatography on silica gel to give 4-(4-bromo-5-formylthiophen-3-yl)benzonitrile (600 mg, yield 27%).

Workup

  1. stirringThe mixture was stirred at −78° C. for 15 min.
  2. stirringThe reaction mixture was stirred at −78° C. for 0.5 h
  3. waitat room temperature for 2 h
  4. customThe mixture was quenched with saturated NH4Cl aqueous solution
  5. extractionextracted with EtOAc
  6. concentrationconcentrated
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7e97a7cddd0347b0a78afce9b8580321
Source dataset
uspto-grants-2014_10
Patent number
US08859611B2

Reaction notes

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