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Cesium carbonate → tert-butyl 4-(4-(2-(methylamino)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 522230
Notes
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Reaction equation

HRID 522230 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)=[CH:10][C:3]=12.[CH3:24][NH:25][C:26]1[C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=[CH:28][N:27]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>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.O1CCOCC1>[CH3:24][NH:25][C:26]1[C:31]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][C:9]([C:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=4)=[CH:10][C:3]=23)=[CH:30][CH:29]=[CH:28][N:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 72218845N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2-amineHCID 118274390tert-butyl 4-(4-bromo-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 118274083
tert-butyl 4-(4-(2-(methylamino)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Example 135D (170 mg, 0.45 mmol), N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (105 mg, 0.45 mmol), bis(triphenylphosphine)palladium(II) chloride (31 mg, 0.045 mmol), tricyclohexylphosphine (13 mg, 0.045 mmol) and cesium carbonate (443 mg, 1.34 mmol) in a round bottom flask was purged with nitrogen. Dioxane (10 mL) was added and the mixture was heated at 100° C. overnight. After cooling, the mixture was triturated with dichloromethane (200 mL) and filtered. The filtrate was concentrated and the residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane) to provide the title compound. MS (ESI+) m/z 406 (M+1).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was triturated with dichloromethane (200 mL)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ffaee0bba07147e3aa9536e63fd3dd65
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09328112B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes