Methyl 4-(bromomethyl)benzoate → (1R,2S)-4-((2-(4-fluorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)benzoic acid

HRID 1805366Notes

Reaction equation

HRID 1805366 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]2[C@:22]3([C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][C:23]3=[O:31])[CH2:21]2)=[CH:16][CH:15]=1>>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C@H:20]2[C@@:22]3([C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH2:10][C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:12])=[CH:5][CH:6]=4)[C:23]3=[O:31])[CH2:21]2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 67233318HCID 67233318, compound

Product 1

HCID 58305348(1R,2S)-4-((2-(4-fluorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)benzoic acid

Procedure

The title compound was prepared in analogy to Example 1 starting from 4-bromomethyl-benzoic acid methyl ester (commercially available), (1R,2S) and (1S,2R)-2-(4-fluorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C24H18FlNO3: 387, observed (M+H)+: 388.1 1H NMR (400 MHz, DMSO-d6) δppm 2.05-2.14 (m, 1 H) 2.30-2.40 (m, 1 H) 3.21 (t, 2 H) 5.09 (s, 2 H) 6.10 (d, 1 H) 6.70 (t, 1 H) 6.92 (d, 1 H) 7.07 (t, 1 H) 7.11-7.20 (m, 2 H) 7.31-7.38 (m, 2 H) 7.44 (d, 2 H) 7.93 (d, 2 H).

Sources & evidence

ORD record
ord-7a70cf097bfd4756a3071198e9e0b1ed
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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