Ethanol → HCID 66803463, compound

HRID 1843823Notes

Reaction equation

HRID 1843823 reaction equation
C([O-])([O-])=O.[Na+].[Na+].C(O)C.Br[C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][NH:17][C:18]2=[O:21])=[CH:13][CH:12]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>CCCCCC.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(OC(=O)C)C.C1(C)C=CC=CC=1>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][NH:17][C:18]3=[O:21])=[CH:13][CH:12]=2)=[CH:25][CH:24]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 250673307-Bromo-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 66803463HCID 66803463, compoundYield 94.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

1M Na2CO3 (211.8 mg, 2.0175 mmol) was added to a mixture of ethanol (10 mL) and toluene (10 mL) previously degassed with argon for 30 minutes. The reaction mixture was degassed with argon for a further 20 minutes. This was followed by the addition of 7-bromo-3,4-dihydro-2H-isoquinolin-1-one (I-3e: 200 mg, 0.877191=4 (4-fluoro-phenyl)-dihydroxy-borane (245 mg, 1.7543 mmol) and Pd(PPh3)4 (20.2 mg, 0.01754 mmol). The resulting mixture was stirred at 110° C. for 5 hours. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was cooled to room temperature, filtered and the filtrate was concentrated under reduced pressure. Purification by column chromatography on silica gel (40% ethylacetate in hexane) afforded 200 mg of the product (94.7% yield).

Workup

  1. custompreviously degassed with argon for 30 minutes
  2. customThe reaction mixture was degassed with argon for a further 20 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification by column chromatography on silica gel (40% ethylacetate in hexane)

Sources & evidence

ORD record
ord-2220939046ca41ac9ab1d68c17e9cede
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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