Isatin → Ethyl 2-(5-chloro-2,3-dioxoindolin-1-yl)acetate

HRID 545775Notes

Reaction equation

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

Participants

Reactant 4

HCID 7054Isatin

HCID 7748Ethyl bromoacetate

HCID 872035-chloro-1H-indole-2,3-dione

HCID 22636989(2-Bromoethyl)cyclopropane

Product 1

HCID 28492634Ethyl 2-(5-chloro-2,3-dioxoindolin-1-yl)acetate

Procedure

Following the procedure as described in PREPARATION 2A, and making non-critical variations to replace isatin with 5-chloro-1H-indole-2,3-dione, and (2-bromoethyl)cyclopropane with ethyl 2-bromoacetate, the title compound was obtained (98%) as solid: 1H NMR (300 MHz, CDCl3) δ 7.60 (d, 1H), 7.54 (dd, 1H), 6.74 (d, 1H), 4.46 (s, 2H), 4.23 (q, 2H), 1.27 (t, 3H); MS (ES+) m/z 268.6 (M+1).

Sources & evidence

ORD record: ord-b538101d7a944aa08b9cc9acaa4fe6e7
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935721B2

Reaction notes

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