Sodium Carbonate → 5-(2-Fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 1432326Notes

Reaction equation

HRID 1432326 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[C:12]([C:20]#[N:21])=[CH:11]2)(=O)=O)C=CC=CC=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>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>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:17]1[CH:18]=[C:13]2[C:12]([C:20]#[N:21])=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27343542-Fluorophenylboronic acidHCID 689524475-Bromo-1-(phenylsulfonyl)-1h-pyrrolo[2,3-b]pyridine-3-carbonitrile

Product 1

HCID 112186085-(2-Fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrileYield 38%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Compound 10 was synthesized according to the procedure used for the preparation of 9 using 8 (40.0 mg, 0.11 mmol), 2-fluorophenylboronic acid (23.2 mg, 0.11 mmol), PdCl2(PPh3)2 (7.8 mg, 0.011 mmol), LiCl (14.0 mg, 0.33 mmol), 1M Na2CO3 (276 mL), EtOH (0.66 mL) and toluene (0.66 mL) with refluxing for 1 h. Obtained 10 (9.9 mg, 38%) as a white solid; 1H NMR (400 MHz, CDCl3+4 drops d4-MeOH) δ 8.54 (t, J=1.9 Hz, 1H), 8.25 (dd, J=2.0, 1.3 Hz, 1H), 7.89 (s, 1H), 7.46 (dt, J=7.7, 1.8 Hz, 1H), 7.37 (m, 1H), 7.30-7.10 (m, 2H).

Workup

  1. customCompound 10 was synthesized
  2. temperaturewith refluxing for 1 h

Sources & evidence

ORD record
ord-ab02ae3817644f2991e23f0571f6dbfc
Source dataset
uspto-grants-2009_11
Patent number
US07612086B2

Reaction notes

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