Cesium carbonate → HCID 58020100, compound

HRID 1632053Notes

Reaction equation

HRID 1632053 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:5][N:6]1[CH:10]=[N:9][CH:8]=[N:7]1.[N:16]1[O:20][N:19]=[C:18]2[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:17]=12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[CH3:15][O:14][C:13]1[CH:12]=[CH:11][C:4]([CH2:5][N:6]2[CH:10]=[N:9][CH:8]=[N:7]2)=[CH:3][C:2]=1[C:22]1[CH:23]=[CH:24][C:17]2[C:18]([CH:21]=1)=[N:19][O:20][N:16]=2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 4672597Benzo[C][1,2,5]Oxadiazole-5-Boronic AcidHCID 58020209HCID 58020209, compound

Product 1

HCID 58020100HCID 58020100, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 1-(3-Bromo-4-methoxy-benzyl)-1H-[1,2,4]triazole (I-104, 402 mg, 1.50 mmol), benzo[1,2,5]oxadiazole-5-boronic acid (I-105, 246 mg, 1.50 mmol), palladium(0) bis(dibenzylideneacetone) (43 mg, 0.075 mmol), and triphenyl phosphine (39.3 mg, 0.15 mmol) in dimethylformamide (15 mL) and 1 M aqueous cesium carbonate (4.5 mL, 4.5 mmol) was heated to 85° C. with stirring overnight. The solvent was removed under vacuum and the residue suspended in ethyl acetate (15 mL). The organic suspension was washed with water (3×15 mL) and brine, dried over sodium sulfate, decolorized over activated carbon, filtered, and the solvent removed under vacuum to give crude material. The residue was purified by recyrstalization from dichloromethane (2 mL) and hexanes (10 mL) to give P-481 (180 mg, 39% yield). 1H NMR (400 MHz, CDCl3) δ ppm 3.88 (s, 4H) 5.51 (s, 2H) 7.06 (d, J=7.8 Hz, 1H) 7.41-7.54 (m, 3H) 7.59 (d, J=9.3 Hz, 1H) 7.71-8.03 (m, 3H) 8.25 (s, 1H) 9.34 (br. s., 1H), LCMS=95.7% purity.

Workup

  1. customThe solvent was removed under vacuum
  2. washThe organic suspension was washed with water (3×15 mL) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under vacuum
  6. customto give crude material
  7. customThe residue was purified by recyrstalization from dichloromethane (2 mL) and hexanes (10 mL)
  8. customto give P-481 (180 mg, 39% yield)

Sources & evidence

ORD record
ord-b75700bad3b44ba7909032da6ae5d9cb
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

Loading…