Methyl 5-(bromomethyl)-2-chlorobenzoate → (1R,2S)-2-chloro-5-((2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)benzoic acid

HRID 1805306Notes

Reaction equation

HRID 1805306 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH2:10]Br)[CH:7]=[CH:6][C:5]=1[Cl:12].[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:12][C:5]1[CH:6]=[CH:7][C:8]([CH2:10][N:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@:23]3([CH2:22][C@H:21]3[C:18]3[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=3)[C:24]2=[O:32])=[CH:9][C:4]=1[C:3]([OH:2])=[O:13]

Participants

3

Reactant 2

HCID 57944070Methyl 5-(bromomethyl)-2-chlorobenzoateHCID 58305306(1R,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53246913(1R,2S)-2-chloro-5-((2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)benzoic acid

Procedure

The title compound was prepared in analogy to Example 1 starting from 5-Bromomethyl-2-chloro-benzoic acid methyl ester (commercially available), (1S,2R) and (1R,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C24H17Cl2NO3: 437, observed (M+H)+: 438.3. 1H NMR (400 MHz, DMSO-d6) δppm 2.07-2.15 (m, 1 H) 2.39 (dd, J=7.83, 5.05 Hz, 1H) 3.20 (t, J=8.72 Hz, 1 H) 5.06 (s, 2 H) 6.16 (d, J=7.58 Hz, 1 H) 6.73 (t, J=7.58 Hz, 1 H) 6.97 (d, J=7.83 Hz, 1 H) 7.09 (t, J=7.83 Hz, 1 H) 7.28-7.40 (m, 4 H) 7.43-7.57 (m, 2 H) 7.73 (s, 1 H).

Sources & evidence

ORD record
ord-cddc47d65e7c4989abfe73f915fc27ed
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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