Sodium Carbonate → HCID 25226755、化合物

HRID 1802482ノート

反応式

HRID 1802482 の反応式
Br[C:2]1[CH:30]=[CH:29][C:5]2[N:6]=[C:7]([NH:15][C:16]3[C:21]([Cl:22])=[CH:20][C:19]([C:23]4[NH:27][N:26]=[CH:25][CH:24]=4)=[CH:18][C:17]=3[Cl:28])[C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.[OH:31][C:32]([CH3:39])([CH3:38])/[CH:33]=[CH:34]/B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:28][C:17]1[CH:18]=[C:19]([C:23]2[NH:27][N:26]=[CH:25][CH:24]=2)[CH:20]=[C:21]([Cl:22])[C:16]=1[NH:15][C:7]1[C:8]2[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=2[C:4]2[CH:3]=[C:2](/[CH:34]=[CH:33]/[C:32]([OH:31])([CH3:39])[CH3:38])[CH:30]=[CH:29][C:5]=2[N:6]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 57416265[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]boronic acidHCID 59435999HCID 59435999、化合物

生成物 1

HCID 25226755HCID 25226755、化合物

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of 9-bromo-5-{[2,6-dichloro-4-(1H-pyrazol-5-yl)phenyl]amino}benzo[c]-2,6-naphthyridin-1(2H)-one (Example 100, Step 4) (125 mg, 0.25 mmol) in THF (4 mL) was added [(1E)-3-hydroxy-3-methylbut-1-en-1-yl]boronic acid (65 mg, 0.45 mmol), Pd(Ph3P)4 (58 mg, 0.05 mmol) and sodium carbonate (0.125 mL, 0.25 mmol, 2M in water). The reaction was heated to 80° C. for 16 h. The reaction was diluted with ethyl acetate and washed with water. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in THF and methanol, filtered and purified by reverse phase HPLC to afford the title compound.

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in THF
  6. filtrationmethanol, filtered
  7. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-e61c32326e714ab68ce608f31807aeaf
出典データセット
uspto-grants-2013_01
特許番号
US08349865B2

反応ノート

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