Sodium Carbonate → HCID 20814970、化合物

HRID 896655ノート

反応式

HRID 896655 の反応式
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=1.Br[C:22]1[CH:23]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O.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>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:22]2[CH:23]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:25]=[C:26]3[C:31]=2[N:30]=[CH:29][CH:28]=[CH:27]3)[CH:6]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 110977913-(2-Methoxy-2-oxoethyl)phenylboronic acid, pinacol esterHCID 218655558-Bromo-6-isopropyl-quinoline

生成物 1

HCID 20814970HCID 20814970、化合物

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
21 °C

実験手順

A solution of [3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester from Step 2 (4 g, 14 mmol), 8-bromo-6-isopropylquinoline (3 g, 12 mmol), Na2CO3 (2M, 18 mL, 36 mmol) and Pd(PPh3)4 (692 mg, 0.6 mmol) in DMF (250 mL) was heated at 80° C. under N2 for 18 h. The resulting reaction mixture was cooled to 21° C. and diluted with water and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 80:20) provided the [3-(6-Isopropyl-quinolin-8-yl)-phenyl]-acetic acid methyl ester compound.

後処理

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 80:20)

出典と根拠

ORDレコード
ord-5b287d9b692446beb1cf3e469962ecf2
出典データセット
uspto-grants-2005_07
特許番号
US06919353B2

反応ノート

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