Potassium Carbonate → [4-(1,3-Benzoxazol-2-yl)-2-methylphenyl]acetonitrile

HRID 7686

Reaction equation

HRID 7686 reaction equation
CB(O)O.[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[C:16](Br)[CH:15]=1.[C:24]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[C:16]([CH3:24])[CH:15]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 139377Methylboronic AcidHCID 10236618[4-(1,3-Benzoxazol-2-yl)-2-bromophenyl]acetonitrile

Product 1

HCID 10214599[4-(1,3-Benzoxazol-2-yl)-2-methylphenyl]acetonitrile

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methane boronic acid (57.6 mg, 0.96 mmol), [4-(1,3-benzoxazol-2-yl)-2-bromophenyl]acetonitrile (example 1) (200 mg, 0.64 mmol), dichlorobis(triphenylphosphine)palladium(II) (22.4 mg, 0.032 mmol), triphenylphosphine (17 mg, 0.064 mmol), and potassium carbonate (177 mg, 1.3 mmol) in degassed DME/H2O (5:1, 12 mL) was heated at 80° C. for 18 h. The mixture was cooled to rt, the two layers were separated and the aqueous layer was extracted with EtOAc (3×). The organics were combined, dried over Na2SO4 and evaporated to dryness to give a brown solid. Purification of the crude solid by flash chromatography on silica gel eluting with a gradient of EtOAc:hexanes (0 to 40 min: 0 to 25% EtOAc) afforded the desired [4-(1,3-benzoxazol-2-yl)-2-methylphenyl]acetonitrile as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.14 (s, 1H), 8.11 (d, 1H), 7.78 (m, 1H), 7.60 (m, 1H), 7.54 (d, 1H), 7.38 (m, 2H), 3.76 (s, 2H), 2.45 (s, 3H). MS (ESI) 249 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customthe two layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (3×)
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customto give a brown solid
  7. customPurification of the crude solid by flash chromatography on silica gel eluting with a gradient of EtOAc

Sources & evidence

ORD record
ord-99598980dcbc49b2980aba4c026922bd
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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