Sodium Carbonate → (E)-3-Cyclopentyl-2-[4-(pyridin-3-ylmethylsulfanyl)-phenyl]-acrylic acid ethyl ester

HRID 2103635Notes

Reaction equation

C([O-])(=O)C.[K+].CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.Br[C:25]1[CH:30]=[CH:29][C:28]([S:31][CH2:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:27][CH:26]=1.[CH2:39]([O:41][C:42](=[O:51])/[C:43](/Br)=[CH:44]/[CH:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1)[CH3:40].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.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]>[CH2:39]([O:41][C:42](=[O:51])/[C:43](/[C:25]1[CH:30]=[CH:29][C:28]([S:31][CH2:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:27][CH:26]=1)=[CH:44]/[CH:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1)[CH3:40]

Participants

Conditions

Temperature: 80 °C

Procedure

Following the method of example 6a, reaction of potassium acetate (1.1 g, 10.7 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (1 g, 3.9 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.28 g, 0.35 mmol) and 3-(4-bromo-phenylsulfanylmethyl)-pyridine (1 g, 3.6 mmol) in DMF (8.9 ml), stirred for 2.5 h at 80° C., and addition of (Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl ester (1.8 g, 7.1 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.14 g, 0.18 mmol) and 2 M aqueous sodium carbonate solution (8.9 ml), stirred at 80° C. over night affords the title compound as a yellow oil (0.8 g). MS (m/e): 368 (M+H).

Workup

stirringstirred at 80° C. over night

Sources & evidence

ORD record: ord-75212a81be82493e8bfcecc31da60e84
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576108B2

Reaction notes

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