Isatin → ethyl (4-bromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate

HRID 425503Notes

Reaction equation

N1C2C(=CC=CC=2)C(=O)C1=O.[Br:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15](=[O:23])[C:16](=[O:22])[NH:17]2.BrCCC1CC1.Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[Br:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15](=[O:23])[C:16](=[O:22])[N:17]2[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

Reactant 4

HCID 7054Isatin

HCID 7748Ethyl bromoacetate

HCID 45000124-Bromoisatin

HCID 22636989(2-Bromoethyl)cyclopropane

Product 1

HCID 28492473ethyl (4-bromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate

Procedure

Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 4-bromoisatin and (2-bromoethyl)cyclopropane with ethyl bromoacetate, the title compound was obtained as a yellow solid (68%): 1H NMR (300 MHz, CDCl3) δ 7.39 (t, 1H), 7.27(dd, 1H), 6.71 (dd, 1H), 4.47 (s, 2H), 4.23 (q, 2H), 1.27 (t, 3H); MS (ES+) m/z 312 (M+1), 314 (M+1), 334 (M+23) 336 (M+23).

Sources & evidence

ORD record: ord-38c8d5db552b477e8d9385b7cf784229
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106087B2

Reaction notes

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