Potassium Phosphate, Tribasic → HCID 86714102, compound

HRID 576441Notes

Reaction equation

HRID 576441 reaction equation
Cl[C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[C:5]([CH:11]2[C@H:16]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@@H:15]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:14]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@@H:13]([CH2:41][O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[O:12]2)=[CH:4][C:3]=1[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][CH2:58][CH3:59])=[CH:53][CH:52]=1.[CH:60]1(B(O)O)[CH2:62][CH2:61]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:60]1([C:2]2[C:10]3[O:9][CH2:8][CH2:7][C:6]=3[C:5]([CH:11]3[C@H:16]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C@@H:15]([O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C@H:14]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C@@H:13]([CH2:41][O:42][CH2:43][C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[O:12]3)=[CH:4][C:3]=2[CH2:50][C:51]2[CH:52]=[CH:53][C:54]([O:57][CH2:58][CH3:59])=[CH:55][CH:56]=2)[CH2:62][CH2:61]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86714103HCID 86714103, compound

Product 1

HCID 86714102HCID 86714102, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 7-chloro-6-(4-ethoxybenzyl)-4-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)-2,3-dihydrobenzofuran (235 mg, 0.290 mmole) in toluene (10 mL) were added cyclopropylboronic acid (49.8 mg, 0.580 mmole), Pd(OAc)2 (19.5 mg, 0.0290 mmole), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (23.8 mg, 0.0580 mmole), and K3PO4 (246 mg, 1.16 mmole). The resulting solution was stirred at 110° C. overnight, diluted with water and extracted with ethyl acetate. The organic layer was washed with water then brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the title compound (102 mg, 43%) as a yellow gum.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on Biotage® purification apparatus

Sources & evidence

ORD record
ord-4d87a864307447b7a2689db93bb67798
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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