Sodium Carbonate → HCID 68515932, compound

HRID 1716327Notes

Reaction equation

HRID 1716327 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:17][CH2:16][CH2:15][CH2:14][N:13]([O:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]2=[O:38])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=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>[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([C:2]2[CH:3]=[CH:4][C:5]([S:8]([CH:11]3[CH2:17][CH2:16][CH2:15][CH2:14][N:13]([O:18][C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:12]3=[O:38])(=[O:9])=[O:10])=[CH:6][CH:7]=2)=[CH:43][CH:42]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 68513003HCID 68513003, compound

Product 1

HCID 68515932HCID 68515932, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The mixture of 3-(4-Bromo-benzenesulfonyl)-1-trityloxy-azepan-2-one prepared from step F (10.1 mg, 0.0171 mmol), 4-Methoxybenzeneboronic acid (10.2 mg, 0.0671 mmol) and Pd(PPh3)4 (3.1 mg, 0.00268 mmol) in 2.0 ml of toluene was added 0.4 ml of saturated Na2CO3 aqueous solution and the resulting mixture was stirred and heated to reflux for 4 hours. The reaction mixture was filtered through celite and diluted with EtOAc and water. The organic phase was washed sequentially with water and saturated NaCl solution, and then dried over anhydrous Na2SO4. The EtOAc solution was concentrated under reduced pressure to give a crude material, which was then purified by a column chromatography (0˜30% EtOAc in hexane). MS: 618.2 (M+H)+, 640.2 (M+Na)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. additiondiluted with EtOAc and water
  5. washThe organic phase was washed sequentially with water and saturated NaCl solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationThe EtOAc solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-afadd75107ee4336bb7b78921f75ce44
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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