Nitrogen → 2-[2-(2-Methyl-propenyl)-3-trifluoromethyl-benzoylamino]-indan-2-carboxylic acid ethyl ester

HRID 1047959Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=2I)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[CH3:29][C:30]([CH3:41])=[CH:31]B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+].N#N>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=2[CH:29]=[C:30]([CH3:41])[CH3:31])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 42-(2-Iodo-3-trifluoromethyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (A8) (500 mg, 1.10 mmol) and 2-methyl-1-propenyl boronic acid pinacol ester (400 mg, 2.20 mmol) in dioxane (20 mL) is added dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium (II) DCM adduct (71.8 mg, 8.2% mmol) and 2M aqueous solution of K2CO3 (1.65 mL, 3.30 mmol). The resulting reaction mixture is filled in with N2, heated to 100° C. and stirred continuously overnight. 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 (396) as light brown oil (100 mg, 21%).

Workup

customThe resulting reaction mixture
customReaction mixture
filtrationis 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-b3cabbe8ba3641beb622bce17f4604ea
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569535B2

Reaction notes

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