Sodium Carbonate → HCID 24831457, compound

HRID 2191083Notes

Reaction equation

HRID 2191083 reaction equation
Br[C:2]1[C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:5]=2[S:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.[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>[N:12]1([C:3]2[S:4][C:5]3[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]=3[C:2]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 24831456HCID 24831456, compound

Product 1

HCID 24831457HCID 24831457, compoundYield 19.1%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
85 °C

Procedure

To a stirred solution of Example 3 (0.16 g, 0.50 mmol) and Pd(PPh3)4 (0.06 g, 0.05 mmol) in DME (5 mL) was added phenylboronic acid (0.07 g, 0.60 mmol) and aqueous 2M Na2CO3 solution (0.50 mL). The reaction mixture was then heated to 85° C. for 18 h before it was poured into brine (50 mL) and extracted with EtOAc (3×100 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 1:9 Et2O/DCM) gave the title compound as a white solid (0.03 g, 19%). δH (DMSO-d6) 7.49-7.32 (5H, m), 3.57-3.54 (4H, m) 2.92-2.89 (4H, m), 2.56-2.44 (4H, m), 2.02-1.94 (2H, m). δ 13C (DMSO-d6) 189.9, 162.8, 153.9, 135.2, 129.6 (2×CH), 129.1 (2×CH), 127.8, 124.0, 123.3, 65.7 (2×CH2), 51.6 (2×CH2), 37.8, 25.8, 24.3. LCMS (ES+) 314.0 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 1:9 Et2O/DCM)

Sources & evidence

ORD record
ord-8c9a83629e2b40068eba8dc880648253
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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