Toluene → HCID 86669230、化合物

HRID 2366835ノート

反応式

HRID 2366835 の反応式
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[CH:7]([NH:15][C:16](=[O:21])[O:17][CH:18]([CH3:20])[CH3:19])[CH2:6][CH:5]1[CH3:22])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH:29]([C:31]1[CH:32]=[C:33](B(O)O)[O:34][CH:35]=1)=[O:30].C1(C)C=CC=CC=1>C(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>[CH3:19][CH:18]([O:17][C:16](=[O:21])[NH:15][C@H:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([C:33]3[O:34][CH:35]=[C:31]([CH:29]=[O:30])[CH:32]=3)[CH:9]=2)[N:4]([C:1](=[O:3])[CH3:2])[C@@H:5]([CH3:22])[CH2:6]1)[CH3:20]

参加物

7

反応物 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27364954-Formylfuran-2-boronic acidHCID 67197028HCID 67197028、化合物

生成物 1

HCID 86669230HCID 86669230、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

実験手順

1-methylethyl (1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation see Example 61) (150 mg, 0.406 mmol) was mixed with potassium carbonate (112 mg, 0.812 mmol), tetrakis(triphenylphosphine)palladium(0) (23.47 mg, 0.020 mmol) and (4-formyl-2-furanyl)boronic acid (68.2 mg, 0.487 mmol, available from Frontier scientific), dissolved in ethanol (1 mL) and toluene (1 mL) and stirred under nitrogen at 90° C. for 2.5 days. The reaction A was partitioned between distilled water (20 mL) and EtOAc (60 mL). The aqueous layer was extracted with EtOAc (2×60 mL) and the organic fractions were combined, washed (brine (50 mL)), dried (sodium sulfate) and evaporated to dryness to give a dark brown solid (184 mg) which was purified using MDAP. Product-containing fractions were evaporated to dryness to give a yellow/brown solid (32 mg).

後処理

  1. customThe reaction
  2. customA was partitioned
  3. distillationbetween distilled water (20 mL) and EtOAc (60 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×60 mL)
  5. washwashed (brine (50 mL))
  6. dry with materialdried (sodium sulfate)
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-108817070d714f35bd14c6ebecf36730
出典データセット
uspto-grants-2014_04
特許番号
US08697725B2

反応ノート

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