Triethylamine → HCID 46206430, compound

HRID 2366477Notes

Reaction equation

HRID 2366477 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:4][C:3]=1[F:24].C(N(CC)CC)C.[C]=O>CO.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:24][C:3]1[CH:4]=[C:5]([C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH:6]=[CH:7][C:2]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 58938109HCID 58938109, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 46206430HCID 46206430, compoundYield 176.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent

Procedure

A mixture of EXAMPLE 87C (1.46 g, 3.7 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride (145 mg) and triethylamine (0.52 mL, 3.7 mmol) in methanol (16 mL) was stirred under 60 psi of carbon monoxide at 100° C. for 1 hour. After cooling to ambient temperature, the mixture was concentrated and the residue purified by flash chromatography on silica gel using a gradient of 10-40% ethyl acetate in hexane to give the title compound as a colorless oil (1.215 g). [α]589=−102.2 (c=0.95 in methanol).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue purified by flash chromatography on silica gel using a gradient of 10-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-04b32ce9e0104c7fb74a9b23e27e2b46
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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