Sodium Hydroxide → 5-(Phenylsulfanyl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1991097Notes

Reaction equation

HRID 1991097 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=[C:13]3[C:12]([C:26]3[CH:27]=[N:28][NH:29][CH:30]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[C:20]1([S:19][C:17]2[CH:18]=[C:13]3[C:12]([C:26]4[CH:30]=[N:29][NH:28][CH:27]=4)=[CH:11][NH:10][C:14]3=[N:15][CH:16]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59128672HCID 59128672, compound

Product 1

HCID 160647935-(Phenylsulfanyl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 59.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7 (130 mg, 0.30 mmol) and 10% aq. sodium hydroxide (2.8 mL) in EtOH (5.8 mL) were heated at 90° C. for 1 h. The solution was cooled, partitioned between CH2Cl2/brine, the layers separated and the aqueous phase extracted with more CH2Cl2 (3×). The combined organic extracts were dried (MgSO4), concentrated and the residue purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give 8 as a white solid (52 mg, 59%); 1H NMR (400 MHz, CDCl3+6 drops CD3OD) δ 7.13 (m, 3H), 7.22 (m, 2H), 7.47 (s, 1H), 7.80 (s, 2H), 8.27 (d, J=2.0 Hz, 1H), 8.38 (d, J=2.0 Hz, 1H).

Workup

  1. temperatureThe solution was cooled
  2. custompartitioned between CH2Cl2/brine
  3. customthe layers separated
  4. extractionthe aqueous phase extracted with more CH2Cl2 (3×)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-98a11a4d58b241189c9b6dd737649465
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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