Sodium Carbonate → HCID 86719551, compound

HRID 2208786Notes

Reaction equation

HRID 2208786 reaction equation
Br[C:2]1[C:11]([N:12]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:19][C:20]1(C)C(C)(C)OB(C=C)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[CH:14]1([N:12]([CH3:13])[C:11]2[C:2]([CH:19]=[CH2:20])=[C:3]([CH:8]=[CH:9][CH:10]=2)[C:4]([O:6][CH3:7])=[O:5])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 70913288HCID 70913288, compound

Product 1

HCID 86719551HCID 86719551, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of methyl 2-bromo-3-(cyclopentyl(methyl)amino)benzoate (1 equiv.) and 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (1.2 equiv.) in dioxane/water mixture (5 mL+1 mL), Na2CO3 (3.6 equiv.) was added and solution purged with argon for 15 min. Then, Pd(PPh3)4 (0.1 equiv.) was added and argon purged for 10 min. and the reaction mixture heated at 100° C. for 2 h. On completion, the reaction mixture was diluted with water and extracted with 10% MeOH/DCM. The combined organic layers were dried over Na2SO4 and solvent removed under reduced pressure to afford crude material which was purified by column chromatography over silica gel to afford the desired methyl 3-(cyclopentyl(methyl)amino)-2-vinylbenzoate.

Workup

  1. customsolution purged with argon for 15 min
  2. customargon purged for 10 min.
  3. additionOn completion, the reaction mixture was diluted with water
  4. extractionextracted with 10% MeOH/DCM
  5. dry with materialThe combined organic layers were dried over Na2SO4 and solvent
  6. customremoved under reduced pressure
  7. customto afford crude material which
  8. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-34f54315e7504e84b9ed02cb774256d8
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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