Nitrogen → 4,7-Difluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

HRID 1047955Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=2I)[CH2:14][C:13]2[C:8](=[C:9]([F:16])[CH:10]=[CH:11][C:12]=2[F:15])[CH2:7]1)=[O:5])[CH3:2].[CH3:28][C:29]([CH3:40])=[CH:30]B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+].N#N>O1CCOCC1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH2:1]([O:3][C:4]([C:6]1([NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=2[CH:28]=[C:29]([CH3:40])[CH3:30])[CH2:14][C:13]2[C:8](=[C:9]([F:16])[CH:10]=[CH:11][C:12]=2[F:15])[CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4,7-difluoro-2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (390) (451 mg, 1 mmol) and 2-methyl-1-propenyl boronic acid pinacol ester (364 mg, 2 mmol) in dioxane (20 mL) was added dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium (II) dichloromethane adduct (65 mg, 8.2% mmol) and 2M aqueous solution of K2CO3 (1.5 mL, 3 mmol). The resulting reaction mixture is filled in with N2, heated to 100° C. and stirred continuously for 4 h. The reaction mixture is filtered and concentrated in vacuo, and the resulting residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0%-50% EtOAc in heptane) to give a pure product (391) as light brown oil (150 mg, 36%).

Workup

customThe resulting reaction mixture
filtrationThe reaction mixture is filtered
concentrationconcentrated in vacuo
customthe resulting residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0%-50% EtOAc in heptane)

Sources & evidence

ORD record: ord-d66d689f1a7647d58f97ab7865e260c7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569535B2

Reaction notes

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