Methyl 6-(bromomethyl)pyridine-2-carboxylate → (1R,2S)-6-((2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)picolinic acid

HRID 1805320Notes

Reaction equation

HRID 1805320 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11]Br)[N:6]=1)=[O:4].[Cl: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>>[Cl: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]([CH2:11][C:7]4[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[CH:9][CH:8]=4)[C:23]3=[O:31])[CH2:21]2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 21471714Methyl 6-(bromomethyl)pyridine-2-carboxylateHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53247544(1R,2S)-6-((2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)picolinic acid

Procedure

The title compound was prepared in analogy to Example 1 starting from 6-bromomethyl-pyridine-2-carboxylic acid methyl ester (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 C23H17ClN2O3: 404, observed (M+H)+: 405.2 1H NMR (400 MHz, DMSO-d6) δppm 2.12 (dd, J=9.09, 4.80 Hz, 1 H) 2.39 (dd, J=8.08, 4.80 Hz, 1 H) 3.22 (t, J=8.59 Hz, 1 H) 5.14 (s, 2 H) 6.15 (d, J=7.33 Hz, 1 H) 6.73 (t, J=7.45 Hz, 1 H) 6.88 (d, J=7.58 Hz, 1 H) 7.00-7.10 (m, 1 H) 7.26 (d, J=1.01 Hz, 1 H) 7.38 (s, 4 H) 7.84-7.98 (m, 2 H).

Sources & evidence

ORD record
ord-aa1096d2d6f4458bae6ff1612723d319
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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