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

HRID 11166

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-5f54c01cc7bf4ef68d7dd7fbd24d551f
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094798B1

Linked notes

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