Toluene → 5-(2-Phenoxy-3-pyridinyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1994205Notes

Reaction equation

HRID 1994205 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)O1.[I-].[Li+].[Cl-].[C:22]([O-:25])([O-])=O.[Na+].[Na+].[C:28]1(C)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>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:25]([C:22]1[C:9]([C:9]2[CH:10]=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)=[CH:10][CH:11]=[CH:12][N:13]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 30165Iodide IonHCID 433294Lithium ChlorideHCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 587309515-(2-Phenoxy-3-pyridinyl)-1H-pyrrolo[2,3-b]pyridineYield 42%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of pinacol ester 31 (200 mg, 0.88 mmol), iodide 32 (390 mg, 1.32 mmol), LiCl (112 mg, 2.63 mmol), PdCl2(PPh3)2 (62 mg, 0.088 mmol), 1.0 M aq. Na2CO3 (2.2 mL, 2.19 mmol) in EtOH (4.0 mL) and toluene (4.0 mL) were refluxed for 5 h. After cooling the reaction mixture was partitioned between EtOAc/brine. The aqueous layer was extracted with more EtOAc (2×) and the combined organic extracts were dried (MgSO4) and concentrated. The residue was purified by silicagel chromatography using EtOAc:hexane (1:1) (gradient elution) to give 33 (106 mg, 42%); 1H NMR (400 MHz, CDCl3) δ 6.26 (bs, 4H), 6.55 (s, 1H), 7.38 (bs, 3H), 7.82 (s, 1H), 8.18 (s, 1H), 8.27 (s, 1H), 8.62 (s, 1H), 10.73 (bs, NH).

Workup

  1. temperaturewere refluxed for 5 h
  2. temperatureAfter cooling the reaction mixture
  3. customwas partitioned between EtOAc/brine
  4. extractionThe aqueous layer was extracted with more EtOAc (2×)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silicagel chromatography

Sources & evidence

ORD record
ord-fa7104e1302348aba209365cd96f3d44
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

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