Toluene → HCID 86669230, compound

HRID 2366835Notes

Reaction equation

HRID 2366835 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 86669230HCID 86669230, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-108817070d714f35bd14c6ebecf36730
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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