Triethylamine → Ethyl (2E)-3-(1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indol-7-yl)acrylate

HRID 1669689

Reaction equation

Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8](=[O:12])[C:7]2([CH3:14])[CH3:13].[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=[CH2:17].C(N(CC)CC)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2/[CH:17]=[CH:16]/[C:15]([O:19][CH2:20][CH3:21])=[O:18])[C:7]([CH3:14])([CH3:13])[C:8]1=[O:12]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 7-bromo-1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one from Step A (112 mg, 0.44 mmol), ethyl acrylate (0.238 mL, 2.20 mmol), triethylamine (0.124 mL, 0.88 mmol), and (PPh3)4Pd (51 mg, 0.044 mmol) in DMF (1.5 mL) was heated at 180° C. in a microwave reactor for 4 h. The reaction mixture was partitioned between CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (50 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude mixture was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc-100:0 to 60:40, to give the title compound. MS: m/z=274 (M+1).

Workup

customThe reaction mixture was partitioned between CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (50 mL)
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude mixture was purified by silica gel chromatography
washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record: ord-a8f73aed4ca44f0a999cb109ce148472
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989624B2

Linked notes

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