Potassium Phosphate, Tribasic → 1,1-Dimethylethyl cyclopropyl({2-methyl-5-[(1E)-3-(methyloxy)-1-propen-1-yl]phenyl}methyl)carbamate

HRID 337556Notes

Reaction equation

HRID 337556 reaction equation
CC([C:5]1([N:8]([CH2:12][C:13]2[CH:18]=[C:17](Cl)[CH:16]=[CH:15][C:14]=2[CH3:20])[C:9](=[O:11])[O-:10])[CH2:7][CH2:6]1)(C)C.CC1(C)C(C)(C)OB(/[CH:29]=[CH:30]/[CH2:31][O:32][CH3:33])O1.CO[C:37]1C=CC=[C:39](OC)[C:38]=1[C:45]1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CCCCO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH:5]1([N:8]([CH2:12][C:13]2[CH:18]=[C:17](/[CH:29]=[CH:30]/[CH2:31][O:32][CH3:33])[CH:16]=[CH:15][C:14]=2[CH3:20])[C:9](=[O:11])[O:10][C:38]([CH3:45])([CH3:39])[CH3:37])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 866516611,1-Dimethylethyl[(5-chloro-2-methylphenyl)methyl]cyclopropylcarbamate

Product 1

HCID 668969781,1-Dimethylethyl cyclopropyl({2-methyl-5-[(1E)-3-(methyloxy)-1-propen-1-yl]phenyl}methyl)carbamate

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

1,1-Dimethylethyl[(5-chloro-2-methylphenyl)methyl]cyclopropylcarbamate (1 eq.) from the previous step and 4,4,5,5-tetramethyl-2-[(1E)-3-(methyloxy)-1-propen-1-yl]-1,3,2-dioxaborolane (1 eq.) were combined in n-BuOH (0.48 M). To this solution was then added tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.02 eq.), [2′,6′-bis(methyloxy)-2-biphenylyl](dicyclohexyl)phosphane (0.08 eq.) and powdered potassium phosphate (2 eq.). The vessel was repeatedly evacuated and back-filled with nitrogen before the resulting suspension was heated at 100° C. for 16 h. The now black suspension was cooled to RT, diluted with EtOAc and filtered through a pad of SiO2. The filtrate was then concentrated in vacuo and the crude product thus obtained was directly subjected to purification by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc). The title compound was isolated as a pale yellow oil.

Workup

  1. customThe vessel was repeatedly evacuated
  2. additionback-filled with nitrogen before the resulting suspension
  3. temperatureThe now black suspension was cooled to RT
  4. additiondiluted with EtOAc
  5. filtrationfiltered through a pad of SiO2
  6. concentrationThe filtrate was then concentrated in vacuo
  7. customthe crude product thus obtained
  8. customwas directly subjected to purification by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-d668d311f5e947deb6a4a6bdd15e946f
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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