Dichloromethane → HCID 178523820, compound

HRID 271368Notes

Reaction equation

HRID 271368 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][CH2:18][C:19](Br)=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=1[B-](F)(F)F.[K+].C(N(CC)CC)C.C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(O)C>[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][CH2:18][C:19]([C:31]2[C:30]([F:29])=[CH:35][CH:34]=[CH:33][C:32]=2[F:36])=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 23677741Potassium (2,6-difluorophenyl)trifluoroboranuideHCID 178523818HCID 178523818, compound

Product 1

HCID 178523820HCID 178523820, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Procedure

A stirred mixture of 1.8 g of trans-[4-(2-bromo-3-phenyl-allyloxy)-cyclohexyl]-carbamic acid benzyl ester, 0.9 g of potassium 2,6-difluorophenyltrifluoroborate (G. A. Molander and B. Biolatto, Journal of Organic Chemistry, (2003), 68, 4302-4314), 1.8 mL of triethylamine, 0.30 g of PdCl2(dppf).CH2Cl2, 50 mL of ethanol was heated to reflux for 12 h. The mixture was cooled and partitioned between 10 mL of water and 50 mL of chloroform The chloroform extract was washed with 50 mL of saturated sodium carbonate, 50 mL of saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluting with a gradient of 10%-25% ethyl acetate in hexane gave 1.1 g of product as a white crystalline solid: MS (m+1)=478.3.

Workup

  1. temperatureto reflux for 12 h
  2. temperatureThe mixture was cooled
  3. custompartitioned between 10 mL of water and 50 mL of chloroform The chloroform
  4. extractionextract
  5. washwas washed with 50 mL of saturated sodium carbonate, 50 mL of saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3984f00843f845e5a669568820cc9005
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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