1,2-Dibromoethane → HCID 58305394, compound

HRID 1805337Notes

Reaction equation

HRID 1805337 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][NH:8][CH:9]=1)=[O:4].[CH2:10](Br)[CH2:11]Br.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[C@:23]3([C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:32])[CH2:22]2)=[CH:17][CH:16]=1>>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C@@H:21]2[C@@:23]3([C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]([CH2:10][CH2:11][N:8]4[CH:9]=[C:5]([C:3]([OH:2])=[O:4])[N:6]=[CH:7]4)[C:24]3=[O:32])[CH2:22]2)=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-oneHCID 178418785HCID 178418785, compound

Product 1

HCID 58305394HCID 58305394, compound

Procedure

The title compound was prepared in analogy to Example 81 starting from methyl-imidazole-4-carboxylate, ethylene dibromide (commercially available), (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C22H18ClN3O3: 407, observed (M+H)+: 408.8 1H NMR (400 MHz, MeOD-d4) δppm 2.25 (dd, J=8.59, 1.77 Hz, 2 H) 3.31 (br. s., 1 H) 5.28 (d, J=3.03 Hz, 2 H) 6.12 (d, J=7.58 Hz, 1 H) 6.71-6.85 (m, 1 H) 7.03 (d, J=8.08 Hz, 1 H) 7.12-7.19 (m, 1 H) 7.21-7.29 (m, 2H) 7.30-7.39 (m, 2 H) 7.86-7.99 (m, 1 H) 8.40 (d, J=8.59 Hz, 1 H) 8.74 (d, J=5.31 Hz, 1 H) 8.84 (s, 1 H).

Sources & evidence

ORD record
ord-00f7fc47b04a40f3a6c8e84ef0887790
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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