1,2-Dimethoxyethane → HCID 58257096, compound

HRID 2093792Notes

Reaction equation

HRID 2093792 reaction equation
Br[C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[F-].[Cs+].C[O:14][CH2:15][CH2:16][O:17][CH3:18]>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.CO>[F:10][C:4]1[CH:3]=[C:2]([C:2]2[CH2:8][CH2:7][C:18]3([O:14][CH2:15][CH2:16][O:17]3)[CH2:4][CH:3]=2)[C:8]([CH3:9])=[CH:7][C:5]=1[NH2:6]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 70180404-Bromo-2-fluoro-5-methylaniline

Product 1

HCID 58257096HCID 58257096, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4,4,4,4-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane (532.0 mg, 2.0 mmol), 4-bromo-2-fluoro-5-methylaniline (406.0 mg, 2.0 mmol), tetrakis(triphenylphosphine)palladium(0) (231.1 mg, 0.2 mmol), cesium fluoride (912.0 mg, 6.0 mmol), 1,2-dimethoxyethane (4 mL) and methanol (2 mL) was degassed for 5 min and then heated at 130° C. in a microwave reactor for 15 min. The reaction was concentrated in vacuo, and purified by silica chromatography (EtOAC/Hexanes:3/7) to afford 2-fluoro-5-methyl-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)aniline; ESMS m/z 264.1 (M+H+).

Workup

  1. customwas degassed for 5 min
  2. concentrationThe reaction was concentrated in vacuo
  3. custompurified by silica chromatography (EtOAC/Hexanes:3/7)

Sources & evidence

ORD record
ord-25103c306f534feea38a766be04d9581
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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