Tetrahydrofuran → 4-(2-Chlorophenyl)-6-methyl-9-(methylamino)pyrrolo[3,4-c]carbazole-1,3(2h,6h)-dione

HRID 11166

반응식

HRID 11166 반응식
COB(OC)OC.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:27]2[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:26]=2[C:25]2[C:24]3[CH:23]=[C:22]([NH:33][CH:34]=O)[CH:21]=[CH:20][C:19]=3[N:18]([CH3:36])[C:17]=2[CH:16]=1.O1CCCC1>CO>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:27]2[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:26]=2[C:25]2[C:24]3[CH:23]=[C:22]([NH:33][CH3:34])[CH:21]=[CH:20][C:19]=3[N:18]([CH3:36])[C:17]=2[CH:16]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 8470Trimethyl borateHCID 878991884-(2-Chlorophenyl)-6-methyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-ylformamide

생성물 1

HCID 219808324-(2-Chlorophenyl)-6-methyl-9-(methylamino)pyrrolo[3,4-c]carbazole-1,3(2h,6h)-dione수율 52.3%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

Borane methylsulphide complex (0.074 mL, 0.78 mmol) and trimethylborate (0.089 mL, 0.78 mmol) were added at 0° C. under an atmosphere of nitrogen to a solution of amide (920) (0.105 g, 0.26 mmol) prepared as described in example 469 dry tetrahydrofuran (10 mL) After stirring at 0° C. for 30 min. the solution was allowed to warm to room temperature over 16 h. Methanol (200 mL) was added and the reaction mixture was stirred for 12 h. The solvent was removed under reduced pressure and the yellow residue was purificatied by column chromatography on silica, eluting with petroleum ether:ethyl acetate (100:0 to 0:100) to give (922) as a red solid (0.053 g, 45%), mp 293–296° C. 1H NMR δ [(CD3)2SO] 11.01 (br s, 1H), 8.10 (d, J=2.3 Hz, 1H), 7.69 (s, 1H), 7.57 (dd, J=7.1, 2.0 Hz, 1H), 7.42–7.52 (m, 4H), 7.02 (dd, J=8.8, 2.3 Hz, 1H), 5.61 (q, J=5.2 Hz, 1H), 3.90 (s, 3H), 2.81 (d, J=5.2 Hz, 3H). EIMS found: M+=389.0929, 391.0905. C22H16ClN3O2 requires 389.0931, 391.0902.

후처리

  1. customprepared
  2. temperatureto warm to room temperature over 16 h
  3. stirringthe reaction mixture was stirred for 12 h
  4. customThe solvent was removed under reduced pressure
  5. washeluting with petroleum ether:ethyl acetate (100:0 to 0:100)

출처 및 근거

ORD 기록
ord-5f54c01cc7bf4ef68d7dd7fbd24d551f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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