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

HRID 2114062Notes

Reaction equation

HRID 2114062 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[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:21]([N:40]1[CH:44]=[C:43](B(O)O)[CH:42]=[N:41]1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].[Li+].[Cl-]>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.C1(C)C=CC=CC=1.CCO>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=[C:13]3[C:12]([C:43]3[CH:42]=[N:41][N:40]([C:21]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:44]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 22031737(1-Trityl-1H-pyrazol-4-yl)boronic acidHCID 242292401-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 104167581-Benzenesulfonyl-5-bromo-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 57.2%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 46 (1 g, 2.16 mmol), EtOH (14 mL), toluene (14 mL), 1-trityl-1H-pyrazole-4-boronic acid (767 mg, 2.16 mmol), 1M aq. Na2CO3 (5.4 mL, 5.4 mmol), LiCl (275 mg, 6.5 mmol) and PdCl2(PPh3)2 (75 mg, 0.108 mmol) was refluxed for 1 h 45 min. The reaction mixture was concentrated to afford a pale yellow solid. The solid was purified by silicagel chromatography (Si 50 g column) using 30% ethyl acetate in hexane as eluent (gradient elution) to give the product 47 (798 mg, 57%) as a pale yellow solid; 1H NMR (400 MHz, CDCl3) δ 7.18-7.23 (m, 6H), 7.33-7.37 (m, 9H), 7.47 (t, J=15.6, 7.4 Hz, 2H), 7.57-7.60 (m, 2H), 7.74 (s, 1H), 7.91 (s, 1H), 7.95 (d, J=2.1 Hz, 1H), 8.15-8.18 (m, 2H), 8.46 (d, J=2.2 Hz, 1H).

Workup

  1. temperaturewas refluxed for 1 h 45 min
  2. concentrationThe reaction mixture was concentrated
  3. customto afford a pale yellow solid
  4. customThe solid was purified by silicagel chromatography (Si 50 g column)
  5. wash(gradient elution)

Sources & evidence

ORD record
ord-bd6d0e766554458182d1b506f60c98b7
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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