(1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one → HCID 53245851, compound

HRID 1805340Notes

Reaction equation

HRID 1805340 reaction equation
C[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[C:4](CC)[C:3]=1I.[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]([C:3]4[CH:4]=[C:5]([CH:9]=[CH:10][CH:2]=4)[C:6]([OH:8])=[O:7])[C:24]3=[O:32])[CH2:22]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 67232941(1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-oneHCID 86654393HCID 86654393, compound

Product 1

HCID 53245851HCID 53245851, compound

Procedure

The title compound was prepared in analogy to Example 81 starting from methyl-ethyl-3-iodobenzoate (commercially available), (1R,2R) and (1S,2S)-2-(4-chlorophenyl)spiro [cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1 LC/MS m/e calcd. for C23H16ClNO3 389, observed (M+H)+: 390.1. 1H NMR (400 MHz, DMSO-d6) δppm 2.31-2.42 (m, 2 H) 3.42 (t, J=8.72 Hz, 1 H) 6.88 (d, J=7.58 Hz, 1 H) 7.15 (t, J=7.20 Hz, 1 H) 7.22-7.28 (m, 1 H) 7.28-7.36 (m, 3 H) 7.36-7.41 (m, 2 H) 7.60-7.70 (m, 2 H) 7.86 (s, 1 H) 7.93-8.00 (m, 1 H) 13.24 (br. s, 1 H).

Sources & evidence

ORD record
ord-a7ce1babc31d4d61a3e7fb014f4674a4
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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