Cesium carbonate → HCID 66722318, compound

HRID 1640014Notes

Reaction equation

HRID 1640014 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([CH3:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][CH:13]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1.[CH:27](/B(O)O)=[CH:28]/[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC.O>C(OCC)(=O)C.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>[O:11]=[C:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH:27]=[CH:28][CH3:29])[CH:10]=2)[CH2:6][N:7]1[C:12]1[CH:13]=[CH:14][C:15]([CH:18]([CH3:26])[C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 18180031Water 1,2-dimethoxyethaneHCID 57429425HCID 57429425, compound

Product 1

HCID 66722318HCID 66722318, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of tert-butyl 2-(4-(6-bromo-1-oxoisoindolin-2-yl)phenyl)propanoate (0.200 g, 0.48 mmol), cis-1-propene-1-boronic acid (0.413 g, 4.8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.554 g, 0.48 mmol), and cesium carbonate (0.470 g, 1.44 mmol) in 5:2 DME/water (7 mL) was heated in a microwave reactor for 20 min at 120° C. The mixture was cooled to room temperature, then diluted with ethyl acetate (8 mL). The reaction mixture was concentrated and purified by flash chromatography (silica, gradient 1-20%, ethyl acetate/hexanes) afforded tert-butyl 2-(4-(1-oxo-6-(prop-1-enyl)isoindolin-2-yl)phenyl)propanoate (0.144 g, 77%) as a yellow solid: mp 125-130° C.; 1H NMR (500 MHz, CDCl3) δ 7.96-7.80 (m, 2H), 7.75-7.65 (m, 1H), 7.54-7.34 (m, 4H), 6.53-6.33 (m, 1H), 5.93-5.87 (m, 1H), 4.84-4.80 (m, 2H), 3.66-3.60 (m, 1H), 1.94-1.91 (m, 3H), 1.47-1.45 (m, 3H), 1.41 (s, 9H) [6:4 mixture of olefin isomers determined by NMR]; ESI MS m/z 378 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by flash chromatography (silica, gradient 1-20%, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e8600caf65cc40bf90c41ef5c3bd8d48
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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