Potassium Carbonate → Icotinib

HRID 1792760노트

반응식

HRID 1792760 반응식
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[CH:11]=[C:12]4[O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][C:13]4=[CH:14][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:5]=[CH:6][CH:7]=1.C[Si]([C:33]#[CH:34])(C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[C:33]([C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:10]3[CH:11]=[C:12]4[O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][C:13]4=[CH:14][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:5]=[CH:6][CH:7]=1)#[CH:34]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 66111TrimethylsilylacetyleneHCID 10216910(3-Bromo-phenyl)-(7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxa-1,3-diaza-cyclododeca[b]naphthalen-4-yl)-amine2회

생성물 1

HCID 22024915Icotinib수율 10.2%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

실험 절차

(3-Bromo-phenyl)-(7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxa-1,3-diaza-cyclododeca[b]naphthalen-4-yl)-amine (Compound 10) (10 mg, 0.5 mmol) was dissolved in DMF (10 mL). Tetrakis(triphenylphosphine) palladium (20 mg), trimethylsilylacetylene (70 microliter, 0.65 mmol), potassium carbonate (10 mg) and copper (I) iodide (5 mg) was added under nitrogen atmosphere. The reaction mixture was refluxed for about 3 h and then the reaction cooled and concentrated in vacuo, to afford a residue, which was flash chromotographed to provide a white solid (20 mg). ES-MS m/z 392 (MH+).

후처리

  1. temperatureThe reaction mixture was refluxed for about 3 h
  2. temperaturethe reaction cooled
  3. concentrationconcentrated in vacuo
  4. customto afford a residue, which

출처 및 근거

ORD 기록
ord-9e262bb65ec44147a7abef9bcbc36b34
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07078409B2

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