Sodium Carbonate → 1-Benzenesulfonyl-5-morpholin-4-yl-3-(trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 2114071Notes

Reaction equation

HRID 2114071 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:18]=[C:13]3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]([N:45]1[CH:49]=[C:48](B(O)O)[CH:47]=[N:46]1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CCO.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.O.C1(C)C=CC=CC=1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:18]=[C:13]3[C:12]([C:48]3[CH:47]=[N:46][N:45]([C:26]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:49]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 22031737(1-Trityl-1H-pyrazol-4-yl)boronic acidHCID 670515121-Benzenesulfonyl-3-iodo-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 670513961-Benzenesulfonyl-5-morpholin-4-yl-3-(trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 81%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of iodide 55 (0.083 g, 0.18 mmol), (1-trityl-1H-pyrazol-4-yl)boronic acid (0.094 g, 0.27 mmol), PdCl2(PPh3)2 (0.012 g, 0.017 mmol), LiCl (0.022 g, 0.52 mmol) and 1.0 M aqueous Na2CO3 solution (0.442 mL, 0.442 mol) in EtOH (2 mL)-toluene (2 mL) was stirred at 105° C. for 2 hours. The mixture was cooled and the organic layer was poured into water and extracted with AcOEt. The organic extract was washed with brine, dried (MgSO4), and concentrated to afford a syrup. The syrup was purified by means of preparative TLC with hexane:AcOEt as eluent to afford 56 (0.093 g, 81%) as a tan syrup. 1H NMR (400 MHz, CDCl3) δ 2.97-3.02 (m, 4H), 3.77-3.82 (m, 4H), 7.11-7.16 (m, 6H), 7.24-7.29 (m, 8H), 7.35-7.40 (m, 2H), 7.44-7.49 (m, 1H), 7.51 (d, J=0.08 Hz, 1H), 7.61 (s, 1H), 7.86 (d, J=0.08 Hz, 1H), 8.06-8.09 (m, 2H), 8.13 (d, J=0.26 Hz, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with AcOEt
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto afford a syrup
  8. customThe syrup was purified by means of preparative TLC with hexane

Sources & evidence

ORD record
ord-bb7082a4ddde463e9e41ca238e5d6624
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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