Sodium Carbonate → HCID 10166393, compound

HRID 2085660Notes

Reaction equation

HRID 2085660 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18](=[O:34])[C:19]3[CH:24]=[CH:23][C:22](B4OC(C)(C)C(C)(C)O4)=[CH:21][CH:20]=3)(=[O:16])=[O:15])=[CH:10][C:9]=2[N+:35]([O-:37])=[O:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:38][C:39]1[CH:44]=[CH:43][C:42](I)=[CH:41][CH:40]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:38][C:39]1[CH:44]=[CH:43][C:42]([C:22]2[CH:21]=[CH:20][C:19]([C:18]([NH:17][S:14]([C:11]3[CH:12]=[CH:13][C:8]([NH:7][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[C:9]([N+:35]([O-:37])=[O:36])[CH:10]=3)(=[O:16])=[O:15])=[O:34])=[CH:24][CH:23]=2)=[CH:41][CH:40]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 11773TriphenylarsineHCID 17961341HCID 17961341, compound

Product 1

HCID 10166393HCID 10166393, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 3C (105 mg, 0.2 mmol), 4-bromo-1-iodobenzene (140 mg, 0.5 mmol), Pd2(dba)3 (18 mg, 0.04 mmol), triphenylarsine (36 mg, 0.12 mmol) and 1M Na2CO3 (0.5 mL) in dioxane (4 mL) was heated to 95° C. and stirred for 5 hours. The mixture was diluted with ethyl acetate (50 mL), washed sequentially with 1M HCl (5 mL), water (5 mL), and brine (5 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 556 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ8.53 (d, 1H), 8.16 (d, 1H), 7.95 (d, 2H), 7.91 (dd, 1H), 7.68-7.60 (m, 5H), 4.12 (d, 1H), 3.67 (m, 1H), 2.00-1.31 (m, 10H).

Workup

  1. washwashed sequentially with 1M HCl (5 mL), water (5 mL), and brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8ecaf5f0cf6c482b8bacd504f0c3e7b3
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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