Ethyl Acrylate → Ethyl (2E)-3-(2-{[(benzyloxy)carbonyl]amino}-2,3-dihydro-1H-inden-5-yl)acrylate

HRID 1713842Notes

Reaction equation

CCN(C(C)C)C(C)C.[CH2:10]([O:17][C:18](=[O:30])[NH:19][CH:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25](Br)[CH:26]=2)[CH2:21]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH:32]=[CH2:33]>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH2:10]([O:17][C:18]([NH:19][CH:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25](/[CH:33]=[CH:32]/[C:31]([O:35][CH2:36][CH3:37])=[O:34])[CH:26]=2)[CH2:21]1)=[O:30])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of palladium(II) acetate (3 mg, 0.01 mmol), Tri-o-tolylphosphine (7 mg, 0.02 mmol) and DIPEA (0.088 mL, 0.5 mmol) was stirred in MeCN (2 mL) at 60° C. under a nitrogen atmosphere for 20 minutes in a 5 mL microwave vial. Benzyl(5-bromo-2,3-dihydro-1H-inden-2-yl)carbamate (174 mg, 0.5 mmol) and ethyl acrylate (28 μL, 0.25 mmol) were added and the mixture was heated in the microwave at 180° C. for 0.5 h. The mixture was adsorbed onto silica and purified by chromatography with 0-40% EtOAc/isohexane as eluent to give the title compound (105 mg, 57%) as a gum; 1H NMR (CDCl3) δ 1.32 (t, 3H), 2.62-2.88 (m, 2H), 3.12-3.36 (m, 2H), 4.18-4.29 (m, 2H), 4.46-4.62 (m, 1H), 4.76 (d, 1H), 5.09 (s, 2H), 6.32-6.41 (m, 1H), 7.10-7.44 (m, 8H), 7.57-7.68 (m, 1H); MS m/e MH+ 366.

Workup

custompurified by chromatography with 0-40% EtOAc/isohexane as eluent

Sources & evidence

ORD record: ord-1d06240424dc4365bd10dd70e6155558
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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