Cesium carbonate → HCID 58020014, compound

HRID 1632088Notes

Reaction equation

HRID 1632088 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]=[CH:9][N:8]=[CH: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>[N:6]1([CH2:5][C:4]2[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:2]([C:22]3[CH:23]=[CH:24][C:17]4[C:18]([CH:21]=3)=[N:19][O:20][N:16]=4)[CH:3]=2)[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 660598HCID 660598, compoundHCID 4672597Benzo[C][1,2,5]Oxadiazole-5-Boronic Acid

Product 1

HCID 58020014HCID 58020014, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 1-(3-bromo-4-methoxy-benzyl)-1H-imidazole (I-167, 267 mg, 1.00 mmol), benzo[1,2,5]oxadiazole-5-boronic acid (I-105, 164 mg, 1.00 mmol), palladium(0)bis(dibenzylideneacetone) (28.7 mg, 0.050 mmol), and triphenylphosphine (26.2 mg, 0.10 mmol) in dimethylformamide (20 mL) and 1 M aqueous cesium carbonate (3.0 mL, 3.0 mmol) was heated to 85° C. with stirring overnight. The solvent was removed under vacuum and the residue suspended in ethyl acetate (25 mL). The organic suspension was washed with water (3×20 mL) and brine, dried over sodium sulfate, decolorized over activated carbon, filtered, and concentrated under. The residue was purified by silica gel preparatory thin layer chromatography (ethyl acetate:dichloromethane 3:1) to give 10.4 mg of P-006 in 9.1% yield. 1H NMR (400 MHz, CDCl3) 3.86 (s, 3H) 5.13 (s, 2H) 6.93 (s, 1H) 7.01 (d, J=8.32 Hz, 1H) 7.10 (s, 1H) 7.17-7.25 (m, 2H) 7.52-7.62 (m, 2H) 7.78-7.85 (m, 2H) ppm. LCMS=100% purity. APCI (+)=307.1 (M+1).

Workup

  1. customThe solvent was removed under vacuum
  2. washThe organic suspension was washed with water (3×20 mL) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under
  6. customThe residue was purified by silica gel preparatory thin layer chromatography (ethyl acetate:dichloromethane 3:1)

Sources & evidence

ORD record
ord-29b47c2ccac445fea22d60c7ab1b3587
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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