Hydrochloric Acid → HCID 57443273, compound

HRID 2261760Notes

Reaction equation

HRID 2261760 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(=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)[NH:24][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 57443273HCID 57443273, compoundYield 63%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

A mixture of 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (213 mg, 0.910 mmol), 6-bromo-1H-indole-3-carboxylic acid methyl ester (193 mg, 0.759 mmol), tetrakis(triphenylphosphine)palladium(0) (57 mg, 0.046 mmol), DMF (2.7 mL), ethanol (1.34 mL) and 2M aqueous potassium carbonate (1.34 mL) is heated to 100° C. for 60 hours. The reaction is cooled to room temperature, diluted with water and acidified with 1 N HCl. The resulting solution is extracted with ethyl acetate. The combined organic layers are dried over anhydrous magnesium sulfate and concentrated. The residue is purified with flash chromatography eluting with 25 to 40% ethyl acetate/heptane to give the title compound (134 mg, 63%). ES/MS m/e 280.3 (M−1).

Workup

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

Sources & evidence

ORD record
ord-1bece021923b45818a294d1119247698
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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