Sodium Carbonate → HCID 11525014, compound

HRID 2250922Notes

Reaction equation

HRID 2250922 reaction equation
Br[C:2]1[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][C:6]([N:8]([CH:18]([CH3:20])[CH3:19])[NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7].C([O-])([O-])=O.[Na+].[Na+].[CH2:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O)[CH3:34]>COCCOC>[C:25]([C:23]1[CH:22]=[CH:21][C:3]([O:4][CH2:5][C:6]([N:8]([CH:18]([CH3:20])[CH3:19])[NH:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])=[C:2]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH2:33][CH3:34])[CH:24]=1)#[N:26]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 58689917HCID 58689917, compound

Product 1

HCID 11525014HCID 11525014, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of benzoic acid N′-[2-(2-bromo-4-cyano-phenoxy)-acetyl]-N′-isopropyl-hydrazide (200 mg, 0.480 mmol) in DME (3 ml)/2M Na2CO3 (0.840 ml, 1.68 mmol) was treated with 2-ethylphenylboronic acid (144 mg, 0.9608 mmol) and Pd[PPh3]4 (55 mg, 0.048 mmol) in a microwave oven at 150° C. for 10 min. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with 30% ethyl acetate/hexanes to afford the product as a white solid (177 mg, 84%). MS m/e 442.25 (M+H+)

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f50e06847a124a19b30ec78964c377a1
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Reaction notes

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