HCID 67065239, compound → HCID 67065229, compound

HRID 2199581Notes

Reaction equation

HRID 2199581 reaction equation
C[Sn](C)(C)[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([O:8][CH3:9])=[O:7].Br[C:16]1[CH:21]=[C:20]([CH:22]=[CH:23][C:24]2[S:25][CH:26]=[C:27]3[O:32][CH2:31][CH2:30][O:29][C:28]=23)[CH:19]=[CH:18][N:17]=1>C1(C)C=CC=CC=1.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>[CH2:30]1[CH2:31][O:32][C:27]2[C:28](=[C:24]([CH:23]=[CH:22][C:20]3[CH:21]=[CH:16][N:17]=[C:18]([C:3]4[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][N:12]=4)[CH:19]=3)[S:25][CH:26]=2)[O:29]1

Participants

5

Reactant 2

HCID 67065239HCID 67065239, compoundHCID 86671865HCID 86671865, compound

Product 1

HCID 67065229HCID 67065229, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of (12) (95 mg, 0.32 mmol) in toluene (5 mL) was added to a solution of (10) (105 mg, 0.32 mmol) in the same solvent (5 mL). Tetrakis(triphenylphosphine)palladium(0) (34 mg, 0.03 mmol) was added and the resulting mixture was refluxed for 20 min. A brown precipitate was obtained which was collected upon filtration, extensively washed with toluene, and dried under vacuum, yielding the product (8) (65 mg, 53%) which was directly used without further purification in the next step. 1H NMR (500 MHz, CDCl3) δ 8.98 (s, 1H), 8.88 (d, J=4.9 Hz, 1H), 8.65 (d, J=5.1 Hz, 1H), 8.48 (s, 1H), 7.90 (d, J=4.2 Hz, 1H), 7.48 (d, J=16.1 Hz, 1H), 7.37 (d, J=4.4 Hz, 1H), 6.93 (d, J=16.2 Hz, 1H), 6.35 (s, 1H), 4.36-4.34 (m, 2H), 4.28-4.26 (m, 2H), 4.00 (s, 3H).

Workup

  1. temperaturethe resulting mixture was refluxed for 20 min
  2. customA brown precipitate was obtained which
  3. filtrationwas collected upon filtration
  4. washextensively washed with toluene
  5. customdried under vacuum

Sources & evidence

ORD record
ord-db3d8f2822ed4088be69f47457862c5b
Source dataset
uspto-grants-2016_06
Patent number
US09359334B2

Reaction notes

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