Potassium Carbonate → HCID 67148566, compound

HRID 2234066Notes

Reaction equation

HRID 2234066 reaction equation
I[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[N:5]=[N:4][C:3]=1[O:14][CH3:15].[C:16]([O:20][C:21]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH3:32])=[C:24]1B1OC(C)(C)C(C)(C)O1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:16]([O:20][C:21]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH3:32])=[C:24]1[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[N:5]=[N:4][C:3]=1[O:14][CH3:15])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 230924634-Iodo-3-methoxy-6-pyridin-4-yl-pyridazineHCID 67148908tert-butyl 3-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Product 1

HCID 67148566HCID 67148566, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Argon is passed for 30 min through a suspension of 333 mg 4-iodo-3-methoxy-6-pyridin-4-yl-pyridazine, 380 mg 3-methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester, 294 mg potassium carbonate, and 111.6 mg triphenylphosphine in 4.8 ml DME and 2.4 ml water. 24 mg palladium (II) acetate is added and the mixture stirred under reflux for 3 h. The product is isolated by extraction with ethyl acetate and purified by chromatography on silica gel yielding 52.1 mg 2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-methyl-indole-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureunder reflux for 3 h
  2. custompurified by chromatography on silica gel yielding 52.1 mg 2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-methyl-indole-1-carboxylic acid tert-butyl ester

Sources & evidence

ORD record
ord-9789ef1c782b42ce89af64f6230ef92e
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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