Dimethylformamide → HCID 59146047, compound

HRID 1512831Notes

Reaction equation

HRID 1512831 reaction equation
[C:1](Cl)([C:3](Cl)=O)=[O:2].CN(C=O)C.[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([C:22]#[N:23])[CH:21]=1)[NH:18][CH:17]=C2.CCOC(C)=O>C(Cl)Cl>[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([C:22]#[N:23])[CH:21]=1)[NH:18][CH:17]=[C:3]2[CH:1]=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 36962535-fluoro-1H-indole-7-carbonitrile

Product 1

HCID 59146047HCID 59146047, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (COCl)2 (4 mL) in DCM (100 mL) at 0° C. was added a solution of DMF (4 mL) in DCM (50 mL) dropwise. Half an hour later, a solution of 5-fluoro-1H-indole-7-carbonitrile (D132) (7 g) in DCM (100 mL) was added. The reaction was allowed to warm to RT to form a yellow precipitate. After 5 hours the solvent was removed by evaporation, and then THF (100 mL) and 2 M aqueous NaOH (100 mL) solution were added to the residue obtained above. After being stirred for about 1 h, EtOAc (3×200 mL) was added, the organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to afford 5-fluoro-3-formyl-1H-indole-7-carbonitrile (D133) (8 g) as a yellow solid. δH (DMSO-d6, 400 MHz): 7.20 (1H, dd), 7.82 (1H, dd), 8.08 (1H, s), 9.64 (1H, s).

Workup

  1. customto form a yellow precipitate
  2. customAfter 5 hours the solvent was removed by evaporation
  3. additionTHF (100 mL) and 2 M aqueous NaOH (100 mL) solution were added to the residue
  4. customobtained above
  5. customthe organic phase was separated
  6. extractionthe aqueous phase was extracted with EtOAc
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-86b4a477dafd4fc3adc9e5d14b73beb3
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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