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Cesium carbonate → 6-(furan-3-yl)-7-methoxy-4-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]isoquinoline-1,3-dione

HRID 2236718
ノート
印刷プレビュー

反応式

HRID 2236718 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[NH:7][C:6](=[O:15])[C:5]2=[CH:16][NH:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.[O:31]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32]1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].CN(C)C=O>[O:31]1[CH:35]=[CH:34][C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[O:12][CH3:13])[C:8](=[O:14])[NH:7][C:6](=[O:15])[C:5]3=[CH:16][NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]3)=[CH:20][CH:19]=2)=[CH:32]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2734358Furan-3-boronic acidHCID 178486408HCID 178486408、化合物

生成物 1

HCID 1784864126-(furan-3-yl)-7-methoxy-4-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]isoquinoline-1,3-dione収率 68.9%

試薬・触媒・溶媒 2

HCID 11029508
Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A mixture of 6-Bromo-7-methoxy-4-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione (241 mg, 0.51 mmole), N,N-dimethylformamide (2 mL), furan-3-boronic acid (143 mg, 1.28 mmole), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (64 mg, 0.062 mmole), tri(t-butyl)phosphine (25 mg, 0.124 mmole) and cesium carbonate (334 mg, 1.02 mmole) is stirred and heated at 110° C. for one hour, cooled in the refrigerator. The reaction mixture is evaporated to dryness, taken up in 5% methanol in chlororform and passed through a short pad of Florisil eluting with 5% methanol in chloroform. The eluate is evaporated in vacuo and treated with acetonitrile, filtered and dried to give a brown solid 161 mg (68%), mp 198-220° C.; MS (ESI): m/z 459.2, 461.2 (M+H).

後処理

  1. temperaturecooled in the refrigerator
  2. customThe reaction mixture is evaporated to dryness
  3. customThe eluate is evaporated in vacuo
  4. additiontreated with acetonitrile
  5. filtrationfiltered
  6. customdried

出典と根拠

ORDレコード
ord-0f22514c95c6400d88b27d333f50f96a
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07713994B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート