Sodium Carbonate → HCID 22990558, compound

HRID 1169287Notes

Reaction equation

HRID 1169287 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:9]#[N:10])=[CH:4][CH:3]=1.[C:17]1(B(O)O)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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:11]1([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:25]3[C:26]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:22]=[CH:23][CH:24]=3)=[CH:3][CH:4]=2)[C:9]#[N:10])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 11346467HCID 11346467, compound

Product 1

HCID 22990558HCID 22990558, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of Example 1A (3.0 g, 10.8 mmol), 1-naphthylboronic acid (2.04 g, 11.9 mmol), Pd(PPh3)4 (249 mg, 0.22 mmol), and 3M Na2CO3 (9.0 mL, 27 mmol) in toluene (18 mL) was heated to 100° C. in a sealed tube, stirred for 14 hours, cooled to room temperature, and partitioned between water and diethyl ether. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20:1 to 10:1 hexanes/ethyl acetate to provide the desired product.

Workup

  1. custompartitioned between water and diethyl ether
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 20:1 to 10:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-8cca131f3cce4238b39deff7001cf03d
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

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