Dimethylformamide → 2-(4-chloro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester

HRID 489559

반응식

HRID 489559 반응식
P(Cl)(Cl)(Cl)=O.CN([CH:9]=[O:10])C.[CH3:11][O:12][C:13]([C:15]1[C:16]2[CH:17]=[C:18]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[NH:19][C:20]=2[CH:21]=[CH:22][CH:23]=1)=[O:14]>C(Cl)Cl>[CH3:11][O:12][C:13]([C:15]1[C:16]2[C:17]([CH:9]=[O:10])=[C:18]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[NH:19][C:20]=2[CH:21]=[CH:22][CH:23]=1)=[O:14]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 183400022-(4-Chloro-phenyl)-1H-indole-4-carboxylic acid methyl ester

생성물 1

HCID 183400032-(4-chloro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Phosphorous oxychloride (0.42 g, 2.71 mmol) was added to DMF (0.99 g, 13.57 mmol) at 0° C. The resulting colorless solution was added dropwise to a solution of 2-(4-chloro-phenyl)-1H-indole-4-carboxylic acid methyl ester (0.52 g, 1.81 mmol) in 10 mL dry CH2Cl2 at 0° C. The reaction was stirred at 0° C. for 10 min then quenched by addition of 5 mL 2 M NaOAc(aq). The layers were separated and the aqueous layer extracted once with CH2Cl2. The combined organic layers were dried (MgSO4) then concentrated in vacuo leaving anorange oil which crystallized on standing. The crystals were rinsed with CH2Cl2 then dried in vacuo to yield 2-(4-chloro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester, 231 mg (41%) as an off-white solid: m.p. 221-222° C.; 1H NMR (300 MHz, d6-DMSO) δ 3.93 (s, 3H), 7.49 (app t, J=7.5 Hz, 1H), 7.71 (m, 4H), 7.94 (d, J=7.8 Hz, 2H), 9.71 (s, 1H), 13.67 (br s, 1H). MS (electrospray, [M−H]) 312.

후처리

  1. customthen quenched by addition of 5 mL 2 M NaOAc(aq)
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted once with CH2Cl2
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationthen concentrated in vacuo
  6. customleaving anorange oil which
  7. customcrystallized
  8. washThe crystals were rinsed with CH2Cl2
  9. customthen dried in vacuo

출처 및 근거

ORD 기록
ord-e3a528d2883440eb812242968eb86dfa
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977298B2

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