Cesium fluoride → Methyl 4-(2-methyl-1,3-benzoxazol-5-yl)benzoate

HRID 1785760Notes

Reaction equation

HRID 1785760 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.[F-].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[CH3:42][O:43][C:44]([C:46]1[CH:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=1)=[O:45]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([C:49]3[CH:50]=[CH:51][C:46]([C:44]([O:43][CH3:42])=[O:45])=[CH:47][CH:48]=3)=[CH:11][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 295105-Chloro-2-methylbenzoxazoleHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 22730885Methyl 4-(2-methyl-1,3-benzoxazol-5-yl)benzoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A room temperature solution of 5-chloro-2-methyl-1,3-benzoxazole (110 mg, 0.71 mmol), CsF (325 mg, 2.14 mmol), Pd(OAc)2 (6.0 mg, 0.028 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (14 mg, 0.036 mmol) and 4-(methoxycarbonyl)phenylboronic acid (180 mg, 1.0 mmol) in dioxane (4 mL) was stirred for 18 hours and concentrated. The concentrate was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes to provide the desired product. 1H NMR (300, MHz, DMSO-d6) δ 8.06 (d, 2H), 8.03 (d, 1H), 7.90 (d, 2H), 7.78 (d, 2H), 7.71 (dd, 1H), 7.29 (d, 2H), 3.90 (s, 3H), 2.65 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-341a062e93d44bb29485d5cae19b5bb1
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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