Sodium Bicarbonate → 2-[4-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

HRID 1047889Notes

Reaction equation

HRID 1047889 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2Br)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[CH3:26][C:27]1([CH3:38])[C:31](C)(C)OB(C=C(C)C)O1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[CH:26]=[C:27]([CH3:38])[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

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 151484474,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolaneHCID 593141512-(2-Bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593143192-[4-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(2-bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (880 mg, 2.2 mmol), 4,4,5,5-tetramethyl-2-(2-methyl-propenyl)-[1,3,2]dioxaborolane (903 μL, 4.4 mmol) and saturated NaHCO3 solution (4.4 mL) in anhydrous DMF (20 mL) is degassed with N2. While under N2 atmosphere, tetrakis(triphenylphosphine)palladium (196 mg, 10 mol %) is added and the reaction is heated in a 110° C. oil bath for 2 h. The reaction is cooled to room temperature, poured into water (40 mL) and extracted with EtOAc (2×30 mL). The combined organic layers are washed with water (15 mL) and brine (20 mL) then concentrated in vacuo. The residue is purified by flash column chromatography (24 g silica gel, gradient elution: 0-50% EtOAc in heptane) to give product (278) as a reddish-brown viscous oil (764 mg, 92%).

Workup

  1. customis degassed with N2
  2. additionWhile under N2 atmosphere, tetrakis(triphenylphosphine)palladium (196 mg, 10 mol %) is added
  3. temperatureThe reaction is cooled to room temperature
  4. additionpoured into water (40 mL)
  5. extractionextracted with EtOAc (2×30 mL)
  6. washThe combined organic layers are washed with water (15 mL) and brine (20 mL)
  7. concentrationthen concentrated in vacuo
  8. customThe residue is purified by flash column chromatography (24 g silica gel, gradient elution: 0-50% EtOAc in heptane)

Sources & evidence

ORD record
ord-47e3c9d065a242a4952c8c259dfd22cb
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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