Dichloromethane → HCID 69892721, compound

HRID 2121255Notes

Reaction equation

HRID 2121255 reaction equation
[CH3:1][N:2]([C:11](=[O:28])[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19]Br)=[CH:14][C:13]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27])[C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][S:6][CH3:7].C[Sn](C)(C)[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1.ClCCl>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]>[CH3:1][N:2]([C:11](=[O:28])[C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:14][C:13]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27])[C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][S:6][CH3:7]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 108684453-(Trimethylstannyl)pyridineHCID 69892573HCID 69892573, compound

Product 1

HCID 69892721HCID 69892721, compoundYield 25.3%

Reagents, catalysts & solvents 1

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

Procedure

Methyl N-[4-(bromoethyn-1-yl)-2-(2-methylphenyl)benzoyl]methionine (200 mg, 0.43 mmol), trimethyl-3-pyridyltin (89 mg, 0.37 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (15 mg, 0.02 mmol) were heated at 80° C. for 18 h. The mixture was evaporated and chromatographed (50% ethyl acetate in hexane) to give 43 mg of the title compound. MS m/e 459 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.60 (m, 1H), 1.86 (m, 1H), 2.1 (m, 8H), 3.68 (s, 3H), 4.63 (m, 1H), 5.97 (m, 1H), 7.30 (m, 6H), 7.63 (m, 1H), 7.83 (m, 1H), 7.99 (m, 1H), 8.59 (m, 1H), 8.78 (m, 1H).

Workup

  1. customThe mixture was evaporated
  2. customchromatographed (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-01e0c8c483a941589ae3f0a4549051b8
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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