Potassium Carbonate → HCID 91179855, compound

HRID 1716275Notes

Reaction equation

HRID 1716275 reaction equation
[CH2:1]([O:8][N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]([NH:16][S:17]([C:20]2[S:21][C:22](Br)=[CH:23][CH:24]=2)(=[O:19])=[O:18])[C:10]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.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>[CH2:1]([O:8][N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]([NH:16][S:17]([C:20]2[S:21][C:22]([C:32]3[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=3)=[CH:23][CH:24]=2)(=[O:19])=[O:18])[C:10]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 91324961HCID 91324961, compound

Product 1

HCID 91179855HCID 91179855, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(R)-5-Bromo-thiophene-2-sulfonic acid (1-benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl)-amide (100 mg, 0.28 mmol) from example 16 was dissolved in THF (3 mL). (4-Methoxyphenyl) boronic acid (64 mg, 0.42 mmol), potassium carbonate (80 mg, 0.56 mmol) and tetrakis(triphenylphosphine)palladium (16 mg, 0.014 mmol) were added at room temperature. The mixture in a sealed vessel was irradiated in microwave oven at 150° C. for 20 min. The resulting reaction mixture was filtered. The solids were washed with water and 1:1 Ether-hexane, then dried under vacuum to give the desired product (70 mg, 51% yield). MS: 485, 487 (M+H).

Workup

  1. customThe mixture in a sealed vessel was irradiated in microwave oven at 150° C. for 20 min
  2. customThe resulting reaction mixture
  3. filtrationwas filtered
  4. washThe solids were washed with water and 1:1 Ether-hexane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f1692afd16014f04ad3e4211dc2271c2
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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