Potassium Carbonate → Icotinib

HRID 1792760ノート

反応式

HRID 1792760 の反応式
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]

参加物

7

反応物 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)-amine2 回

生成物 1

HCID 22024915Icotinib収率 10.2%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

(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+).

後処理

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

出典と根拠

ORDレコード
ord-9e262bb65ec44147a7abef9bcbc36b34
出典データセット
uspto-grants-2006_07
特許番号
US07078409B2

反応ノート

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