Toluene → HCID 86669230, 화합물

HRID 2366835노트

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HRID 2366835 반응식
[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]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27364954-Formylfuran-2-boronic acidHCID 67197028HCID 67197028, 화합물

생성물 1

HCID 86669230HCID 86669230, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-108817070d714f35bd14c6ebecf36730
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697725B2

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