Sodium Carbonate → HCID 57704850, compound

HRID 607100Notes

Reaction equation

HRID 607100 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:12].[NH4+:13].[OH-].[F:15][C:16]([F:63])([F:62])[C:17]1[CH:18]=[C:19]([C@H:27]2[O:31][C:30](=[O:32])[N:29]([CH2:33][C:34]3[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:35]=3[C:44]3[CH:49]=[C:48](B4OC(C)(C)C(C)(C)O4)[CH:47]=[CH:46][C:45]=3[O:59][CH3:60])[C@H:28]2[CH3:61])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.CCO.O>[F:15][C:16]([F:63])([F:62])[C:17]1[CH:18]=[C:19]([C@H:27]2[O:31][C:30](=[O:32])[N:29]([CH2:33][C:34]3[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:35]=3[C:44]3[CH:49]=[C:48]([C:2]4[CH:7]=[CH:6][C:5]([S:8]([NH2:13])(=[O:10])=[O:9])=[CH:4][C:3]=4[CH3:12])[CH:47]=[CH:46][C:45]=3[O:59][CH3:60])[C@H:28]2[CH3:61])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 14923Ammonium HydroxideHCID 27375034-Bromo-3-methylbenzene-1-sulfonyl chlorideHCID 57704818HCID 57704818, compound

Product 1

HCID 57704850HCID 57704850, compound

Reagents, catalysts & solvents 5

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-bromo-3-methyl-benzenesulfonyl chloride (120 mg, 0.37 mmol) in dioxane (5 ml) at room temperature, concentrated NH4OH (1 ml) was added. The mixture was stirred at room temperature for 4 h. A solution of the title compound from Example 21, Step A (100 mg, 0.14 mmol), sodium carbonate (30 mg, 0.28 mmol), and catalytic amount of tetrakis(triphenylphosphine) palladium (5% mol) in 14 ml of 1:2:4 mixture of water:EtOH:toluene was stirred under reflux for 6 h. The solvents were removed. Water (10 ml) was added. The mixture was extracted with methylene chloride (3×10 ml). The combined methylene chloride layers were washed with brine and dried over sodium sulfate. The title compound was obtained after reverse phase HPLC. 1H NMR (CDCl3, 500 MHz): δ a mixture of 1:1 atopoisomers 7.89 (s, 1H), 7.86 (d, J=7.5 Hz, 1H), 7.79 (d, J=8.0 Hz, 1H), 7.72 (s, 2H), 7.68 (m, 2H), 7.45 (t, J=8.0 Hz, 1H), 7.39 (m, 2H), 7.13 (m, 2H), 5.60 (d, J=8.5 Hz, 0.5H), 5.38 (d, J=8.5 Hz, 0.5H), 5.00 (d, J=16.0 Hz, 0.5H), 4.94 (d, J=16.0 Hz, 0.5H), 4.17 (d, J=16.0 Hz, 0.5H), 3.99 (d, J=16.0 Hz, 0.5H), 3.90 (s, 1.5H), 3.89 (s, 1.5H), 3.84 (m, 1H), 2.42 (s, 1.5H), 2.37 (s, 1.5), 1.75 (br s, 2H), 0.59 (d, J=6.5 Hz, 1.5H), 0.48 (d, J=7.0 Hz, 1.5H). LC/MS (M+1) 747.20.

Workup

  1. temperatureunder reflux for 6 h
  2. customThe solvents were removed
  3. additionWater (10 ml) was added
  4. extractionThe mixture was extracted with methylene chloride (3×10 ml)
  5. washThe combined methylene chloride layers were washed with brine
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-ee87d9cd76a64ea58470a7b1c9b63ad0
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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