3-(Bromomethyl)pyridine → (2R,1S)-2-(4-chlorophenyl)-1'-(pyridin-3-ylmethyl)spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1805330Notes

Reaction equation

HRID 1805330 reaction equation
Br[CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[C@:18]3([C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][C:19]3=[O:27])[CH2:17]2)=[CH:12][CH:11]=1>>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:16]2[C@:18]3([C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:2][C:3]4[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=4)[C:19]3=[O:27])[CH2:17]2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 2459343-(Bromomethyl)pyridineHCID 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53245016(2R,1S)-2-(4-chlorophenyl)-1'-(pyridin-3-ylmethyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Procedure

The title compound was prepared in analogy to Example 78 starting from 3-bromomethyl-pyridine (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 C29H27ClN2O2: 470, observed (M+H)+: 471.2 1HNMR (400 MHz, MeOD-d4) δppm 2.25 (dd, J=8.59, 1.77 Hz, 2 H) 3.31 (br. s., 1 H) 5.28 (d, J=3.03 Hz, 2 H) 6.12 (d, J=7.58 Hz, 1 H) 6.71-6.85 (m, 1 H) 7.03 (d, J=8.08 Hz, 1 H) 7.12-7.19 (m, 1 H) 7.21-7.29 (m, 2 H) 7.30-7.39 (m, 2 H) 7.86-7.99 (m, 1 H) 8.40 (d, J=8.59 Hz, 1 H) 8.74 (d, J=5.31 Hz, 1 H) 8.84 (s, 1 H).

Sources & evidence

ORD record
ord-2ad133c31c7c42aa99c11ca4776e57ac
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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