Ammonium Chloride → 5-bromo-1H-indole-2-carboxamide

HRID 1716688ノート

反応式

HRID 1716688 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.C([N:17](C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH2:17])=[O:13])=[CH:5]2

参加物

7

反応物 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2521375-Bromo-1H-indole-2-carboxylic acid2 回HCID 2724699PyBOP

生成物 1

HCID 47778755-bromo-1H-indole-2-carboxamide収率 53.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-bromo-1H-indole-2-carboxylic acid (4 g, 16.7 mmol) in DMF (50 ml) at room temperature was added diisopropylethylamine (DIPEA) (5.71 ml, 32.8 mmol), PyBOP (13 g, 25.0 mmol) and HOBT (3.39 g, 25.0 mmol). After stirring the mixture for 30 minutes, NH4Cl (1.75 g, 32.8 mmol) was added and the resulting yellow suspension was stirred at room temperature for 6 hours. The reaction was quenched by addition of H2O. The yellow foamy precipitate was discarded and the mother liquor was extracted with EtOAc. The organic layers were combined, washed with NaOH (1M) and brine, dried over Na2SO4, filtered and concentrated. The residue was then dissolved in EtOAc and washed with HCl (1 M) and brine, dried over Na2SO4, filtered and concentrated. The oily residue was triturated with DCM affording, after filtration, 5-Bromo-1H-indole-2-carboxylic acid amideC as a light yellow solid (2.12 g, 53% yield).

後処理

  1. stirringthe resulting yellow suspension was stirred at room temperature for 6 hours
  2. customThe reaction was quenched by addition of H2O
  3. extractionthe mother liquor was extracted with EtOAc
  4. washwashed with NaOH (1M) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue was then dissolved in EtOAc
  9. washwashed with HCl (1 M) and brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe oily residue was triturated with DCM affording

出典と根拠

ORDレコード
ord-f09187a0db224fdeb616f49a38549f85
出典データセット
uspto-grants-2010_09
特許番号
US07803830B2

反応ノート

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