Toluene → HCID 59238607, compound

HRID 1924467Notes

Reaction equation

HRID 1924467 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:9][N:8]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:5]2=[N:6][CH:7]=1.[Cl-].[Li+].[C:28]1(C)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:35]([O-])([O-])=[O:36].[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>[CH3:35][O:36][C:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=1[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:9][N:8]([S:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:18])[C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 59128653HCID 59128653, compound

Product 1

HCID 59238607HCID 59238607, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Procedure

5-Bromo-3-(1-methyl-1H-pyrazol-4-yl)-1-(phenyl sulfonyl)-1H-pyrrolo[2,3-b]pyridine (III-a) (0.25 g, 0.60 mmol), boronic ester (VIb-31) (0.71 g, 3.00 mmol), lithium chloride (50 mg, 1.20 mmol), and Pd(PPh3)2Cl2 (42 mg, 0.060 mmol), in EtOH (1.50 mL), toluene (1.50 mL) and 1.0 M Na2CO3 solution (1.50 mL) were reacted using the general procedure A for the Suzuki reaction. The crude product was purified by PTLC using hexane:EtOAc=1:1 (v/v) as eluent to give (IIa-31) (single isomer) as a yellow oil (81 mg, 30%); 1H NMR (400 MHz, CDCl3) δ 1.67-1.75 (m, 2H), 1.77-1.85 (m, 2H), 2.29-2.38 (m, 4H), 3.46 (s, 3H), 3.98 (s, 3H), 7.45-7.50 (m, 2H), 7.53-7.58 (m, 1H), 7.63 (s, 1H), 7.71 (s, 1H), 7.75 (d, J=0.8 Hz, 1H), 7.93 (d, J=2.0 Hz, 1H), 8.19-8.22 (m, 2H), 8.48 (d, J=2.0 Hz, 1H).

Workup

  1. customfor the Suzuki reaction
  2. customThe crude product was purified by PTLC

Sources & evidence

ORD record
ord-3fac8932d6fa40319deb2cdb34e8d120
Source dataset
uspto-grants-2012_05
Patent number
US08178552B2

Reaction notes

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