Dimethylformamide → HCID 59146047、化合物

HRID 1512831ノート

反応式

HRID 1512831 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 59146047HCID 59146047、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-86b4a477dafd4fc3adc9e5d14b73beb3
出典データセット
uspto-grants-2012_07
特許番号
US08217028B2

反応ノート

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