1,2-Dibromoethene → HCID 53244448, compound

HRID 1805385Notes

Reaction equation

HRID 1805385 reaction equation
Br[CH:2]=[CH:3]Br.[N:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]2[C@:26]3([C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[NH:28][C:27]3=[O:35])[CH2:25]2)=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C@H:24]2[C@@:26]3([C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]([CH2:2][CH2:3][N:14]4[CH2:13][CH2:12][N:11]([C:8]5[CH:9]=[CH:10][N:5]=[CH:6][CH:7]=5)[CH2:16][CH2:15]4)[C:27]3=[O:35])[CH2:25]2)=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 108971,2-DibromoetheneHCID 705171-(4-Pyridyl)piperazineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53244448HCID 53244448, compound

Procedure

The title compound was prepared in analogy to Example 81 starting from dibromo ethylene, 1-(pyridin-4-yl)piperazine (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 C27H27ClN4O: 458, observed (M+H)+: 459.2 1HNMR (400 MHz, MeOD-d4) δppm 1.32 (s, 2 H) 2.02-2.40 (m, 3 H) 3.26 (s, 1 H) 3.47 (d, J=9.09 Hz, 8 H) 4.02 (br. s., 4 H) 4.25 (s, 2 H) 6.11 (d, J=7.33 Hz, 1 H) 6.80 (s, 1 H) 7.12-7.18 (m, 1 H) 7.19-7.27 (m, 3 H) 7.32 (t, J=8.97 Hz, 4 H) 8.27 (d, J=7.83 Hz, 2 H).

Sources & evidence

ORD record
ord-7f4a24c50c574ca985ee6ab3bca89ec9
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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