Water → HCID 86714047, compound

HRID 2206709Notes

Reaction equation

HRID 2206709 reaction equation
Br[CH2:2][C:3]1[CH:11]=[C:10]([C@H:12]2[C@H:17]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@@H:16]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:15]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@@H:14]([CH2:42][O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[O:13]2)[C:6]2[CH2:7][CH2:8]O[C:5]=2[C:4]=1[Cl:51].C([O-])([O-])=O.[K+].[K+].[CH3:58][O:59][C:60]1[CH:65]=[CH:64][C:63](B(O)O)=[CH:62][CH:61]=1.[OH2:69]>CC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:51][C:4]1[C:5]2[O:69][CH2:8][CH2:7][C:6]=2[C:10]([CH:12]2[C@H:17]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C@@H:16]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:15]([O:34][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C@@H:14]([CH2:42][O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[O:13]2)=[CH:11][C:3]=1[CH2:2][C:63]1[CH:64]=[CH:65][C:60]([O:59][CH3:58])=[CH:61][CH:62]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 86714048HCID 86714048, compound

Product 1

HCID 86714047HCID 86714047, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of compound 67 (700 mg, 0.9 mmol), K2CO3 (497 mg, 3.6 mmol) and 4-methoxyphenyl boronic acid (341 mg, 2.25 mmol) in acetone (9.0 mL) and H2O (3.0 mL) was added bis(triphenylphosphine)palladiumchloride (63 mg, 0.09 mmol) at 0° C. under atmosphere of nitrogen. The mixture was stirred at 0° C. for 30 min and then, stirred at room temperature for 16 hours. The mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 68 (340 mg, 46%) as colorless oil.

Workup

  1. stirringstirred at room temperature for 16 hours
  2. customThe mixture was partitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5abcbd09cddf4053abad58c5e599ae0e
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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