Sodium Carbonate → HCID 11713386, compound

HRID 1661531Notes

Reaction equation

HRID 1661531 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@:8]23[C@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:14][C@@H:13]([OH:22])[C@@:12]2([OH:23])[C:11]2[C:24]([O:31][CH2:32][CH3:33])=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[CH:27][C:10]=2[O:9]3)=[CH:4][CH:3]=1.[NH2:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.O1CCOCC1.CS(C)=O.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>[NH2:34][C:35]1[CH:36]=[C:37]([C:2]2[CH:3]=[CH:4][C:5]([C@:8]34[C@H:15]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[CH2:14][C@@H:13]([OH:22])[C@@:12]3([OH:23])[C:11]3[C:24]([O:31][CH2:32][CH3:33])=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[CH:27][C:10]=3[O:9]4)=[CH:6][CH:7]=2)[CH:38]=[CH:39][CH:40]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 57545194HCID 57545194, compound

Product 1

HCID 11713386HCID 11713386, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

51.1 mg (0.10 mmol) of (1R*,3S*,3aR*,8bS*)-3a-(4-bromophenyl)-6,8-diethoxy-3-phenyl-2,3,3a,8b-tetrahydrocyclopenta[b]benzofuran-1,8b-(1H)-diol (Example 8A), 15.5 mg (0.10 mmol) of 3-aminophenyl boronic acid, 10.6 mg (0.10 mmol) of sodium carbonate and 5.8 mg (0.005 mmol) of tetrakis(triphenylphosphine)palladium(0) are heated in a mixture of 0.1 ml of water and 0.5 ml of dioxane at 80° C. under argon overnight. The mixture is then diluted with DMSO and filtered, and the filtrate is purified by preparative HPLC. 17.4 mg (25% of theory) of the product are obtained.

Workup

  1. filtrationfiltered
  2. customthe filtrate is purified by preparative HPLC
  3. custom17.4 mg (25% of theory) of the product are obtained

Sources & evidence

ORD record
ord-e2768dd08945431b8d8ba7809165f9fa
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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