Sodium Carbonate → HCID 11510518, compound

HRID 2250918Notes

Reaction equation

HRID 2250918 reaction equation
Br[C:2]1[CH:24]=[C:23]([F:25])[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+].[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1B(O)O>COCCOC>[F: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:35]=[CH:34][C:33]([F:32])=[CH:38][C:37]=2[F:39])[CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 58689907benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide

Product 1

HCID 11510518HCID 11510518, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of benzoic acid N′-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N′-isopropyl-hydrazide (100 mg, 0.244 mmol) in DME (5 ml)/2M Na2CO3 (0.428 ml, 0.855 mmol) was treated with 2,4-difluorophenylboronic acid (77 mg, 0.489 mmol) and Pd[PPh3]4 (28 mg, 0.0244 mmol) at 90° C. overnight. The reaction mixture was partitioned between water and DCM. 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 a 30-50% ethyl acetate/hexanes gradient to afford the product as solid (90 mg, 82%). MS m/e 443.38 (M+H+)

Workup

  1. customThe reaction mixture was partitioned between water and DCM
  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 a 30-50% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-9ca5a6b86a4446879451fbd814f9c39b
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Reaction notes

Loading…