Sodium Carbonate → HCID 67175440, compound

HRID 1913087Notes

Reaction equation

HRID 1913087 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[O:7]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]([N:19]3[CH:24]4[CH2:25][CH2:26][CH:20]3[CH:21]=[C:22](OS(C(F)(F)F)(=O)=O)[CH2:23]4)=[O:18])=[CH:16][C:11]=2[O:10][CH2:9][CH2:8]1.[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Cl-].[Li+]>[Cl-].[Na+].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.COCCOC.O>[O:7]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]([N:19]3[CH:24]4[CH2:25][CH2:26][CH:20]3[CH:21]=[C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:23]4)=[O:18])=[CH:16][C:11]=2[O:10][CH2:9][CH2:8]1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 86664776HCID 86664776, compound

Product 1

HCID 67175440HCID 67175440, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2 M aqueous Na2CO3 solution (1.0 mL) is added to a flask charged with a stir bar, trifluoro-methanesulfonic acid 8-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-8-aza-bicyclo[3.2.1]oct-2-en-3-yl ester (0.40 g), phenylboronic acid (0.13 g), lithium chloride (87 mg), Pd(PPh3)4 (60 mg), water (2 mL), and 1,2-dimethoxyethane (10 mL) in argon atmosphere. The resulting mixture is stirred at reflux temperature for 4 h. After cooling to ambient temperature, brine is added and the mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and the solvent is removed under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→2:1).

Workup

  1. additioncharged with a stir bar
  2. temperatureat reflux temperature for 4 h
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe combined extracts are dried (Na2SO4)
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→2:1)

Sources & evidence

ORD record
ord-ac27a9e6500045b08fa1431e289c138e
Source dataset
uspto-grants-2013_12
Patent number
US08609690B2

Reaction notes

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