3-Benzyloxy-phenylboronic acid → Carbazole

HRID 498891

Reaction equation

HRID 498891 reaction equation
COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1.OB(O)c1cccc(OCc2ccccc2)c1>CC#N.CS(=O)(=O)[O][Pd]1(<-[NH2]c2ccccc2-c2cccc[c]21)<-[P](C1=CC=C[CH]1[Fe][CH]1C=CC=C1P(c1ccccc1)c1ccccc1)(c1ccccc1)c1ccccc1.O.O=P([O-])([O-])[O-].[K+].[K+].[K+]>COC(=O)/C(C)=C(/c1cccc(OCc2ccccc2)c1)C1CC1.COC(=O)/C(C)=C(\c1cccc(OCc2ccccc2)c1)C1CC1.Nc1ccccc1-c1ccccc1-c1cccc(OCc2ccccc2)c1.Oc1cccc(OCc2ccccc2)c1.c1ccc(COc2cccc(-c3cccc(OCc4ccccc4)c3)c2)cc1.c1ccc2c(c1)[nH]c1ccccc12

Participants

17

Reactant 2

HCID 27343133-Benzyloxy-phenylboronic acidHCID 90357412methyl (E)-3-cyclopropyl-2-methyl-3-(4-methylphenyl)sulfonyloxyprop-2-enoate

Product 10

HCID 6854Carbazole25×HCID 693011,3,5-Trimethoxybenzene25×HCID 138048Benzyl 3-hydroxyphenyl ether25×HCID 27343133-Benzyloxy-phenylboronic acid25×HCID 666712583,3'-Dibenzyloxybiphenyl25×HCID 90357412methyl (E)-3-cyclopropyl-2-methyl-3-(4-methylphenyl)sulfonyloxyprop-2-enoate25×HCID 90357628methyl (E)-3-cyclopropyl-2-methyl-3-(3-phenylmethoxyphenyl)prop-2-enoate25×HCID 90357629(Z)-methyl 3-(3-(benzyloxy)phenyl)-3-cyclopropyl-2-methylacrylate25×HCID 178505365HCID 178505365, compound25×HCID 178507480HCID 178507480, compound25×

Reagents, catalysts & solvents 5

HCID 62657Potassium Phosphate, TribasicReagentHCID 178505365HCID 178505365, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 693011,3,5-TrimethoxybenzeneInternal standard

Conditions

Temperature
25 °C

Procedure

To a 4 ml reaction vial equipped with a magnetic tumble stir disc under N2 atmosphere was charged (E)-methyl 3-cyclopropyl-2-methyl-3- (tosyloxy)acrylate 3-(E) (40.0 mg, 0.129 mmol), (3-(benzyloxy)phenyl)boronic acid 4 (32.3 mg, 0.142 mmol), palladium precatalyst 5 (5.96 mg, 6.44 µmol) and 1,3,5-trimethoxybenzene (2.17 mg, 0.013 mmol). ACN (1000 µl) and water (10 µl) were added and the mixture agitated to dissolve all solids. To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to 10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in preparation for automated dispensing (387 µl, 0.387 mmol). Finally, to a 96-well sample dilution plate was charged 400 µl of a 9:1 mixture of acetonitrile and aqueous pH 3.5 ammonium formate buffer.

Workup

  1. aliquotReaction aliquots were sampled into 96-well dilution plates (Analytical Sales 17P687) capped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075).
  2. additionNo procedure recorded

Sources & evidence

ORD record
ord-14091a23403d4d96bdcbd0a64f981f4d
Source dataset
Development of an automated kinetic profiling system with online HPLC for reaction optimization
Original link
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Linked notes

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