Sodium Carbonate → tert-butyl 4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 79580Notes

Reaction equation

HRID 79580 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:18]1[C:19]([N:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[C:20]2[CH:26]=[CH:25][NH:24][C:21]2=[N:22][CH:23]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[C:19]([N:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]3)=[C:20]3[CH:26]=[CH:25][NH:24][C:21]3=[N:22][CH:23]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 68760498tert-butyl 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 68760091tert-butyl 4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylateYield 66.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

4-Fluorophenylboronic acid (44.0 mg, 0.315 mmol), PS-palladium tetrakis (119 mg, 0.0131 mmol) and 2N sodium carbonate (262 μL, 0.525 mmol) were added to tert-butyl 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (100 mg, 0.262 mmol, see Example 1) in dioxane (1 mL, degassed with Ar). The reaction was heated to 150° C. for 1 hour under microwave irradiation. The reaction was then cooled down and filtered. The filtrate was diluted with DCM and dried with MgSO4. After concentration, the residue was purified by chromatography (SP4, 25+M, water/ACN 90/10→10/90, 20CV) to yield tert-butyl 4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate (69 mg, 66.4% yield) as a solid.

Workup

  1. temperatureThe reaction was then cooled down
  2. filtrationfiltered
  3. additionThe filtrate was diluted with DCM
  4. dry with materialdried with MgSO4
  5. concentrationAfter concentration
  6. customthe residue was purified by chromatography (SP4, 25+M, water/ACN 90/10→10/90, 20CV)

Sources & evidence

ORD record
ord-f0fd674d11c84d37b157ef92245d153d
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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