Hydrochloric Acid → HCID 66704132, compound

HRID 2261841Notes

Reaction equation

HRID 2261841 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[CH:6][C:7]=1B1OC(C)(C)C(C)(C)O1.[CH3:18][O:19][C:20]([C:22]1[C:30]2[C:25](=[CH:26][C:27](Br)=[CH:28][CH:29]=2)[NH:24][CH:23]=1)=[O:21].[C:32](=O)([O-])[O-].[K+].[K+].Cl>O.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.C(O)C.CN(C=O)C>[CH3:18][O:19][C:20]([C:22]1[C:30]2[C:25](=[CH:26][C:27]([C:7]3[CH:6]=[CH:5][C:4]([OH:17])=[CH:3][C:2]=3[CH3:1])=[CH:28][CH:29]=2)[N:24]([CH3:32])[CH:23]=1)=[O:21]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11499811Methyl 6-Bromo-1H-Indole-3-CarboxylateHCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 66704132HCID 66704132, compoundYield 87%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (2.36 g, 10.1 mmol), 6-bromo-1H-indole-3-carboxylic acid methyl ester (1.8 g, 6.71 mmol), tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.26 mmol), DMF (27 mL), ethanol (13.5 mL) and 2M aqueous potassium carbonate (13.5 mL) is heated to 85° C. for 4 hours. The reaction is cooled to room temperature and diluted with water and acidified with 1 N HCl. The resulting solution is extracted with ethyl acetate. The combined organic layers are washed with brine and dried over anhydrous magnesium sulfate and concentrated. The residue is purified with flash chromatography eluting with 25→40% ethyl acetate/heptane to give 1.73 mg (87%) of the title compound.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionThe resulting solution is extracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified with flash chromatography
  7. washeluting with 25→40% ethyl acetate/heptane

Sources & evidence

ORD record
ord-c04c2f93dc734a53b50ad4779b3fbf84
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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