(1R,2S)-2-(1-benzyl-1H-indazol-6-yl)-1'-methylspiro[cyclopropane-1,3'-indolin]-2'-one → (1R,2S)-2-(1H-indazol-6-yl)-1'-methylspiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1410356Notes

Reaction equation

HRID 1410356 reaction equation
N1C2C(=CC=C([C@H]3[C@@]4(C5C(=CC=CC=5)NC4=O)C3)C=2)C=N1.C([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C@H:38]3[C@@:40]4([C:48]5[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=5)[N:42]([CH3:49])[C:41]4=[O:50])[CH2:39]3)[CH:36]=2)[CH:31]=[N:30]1)C1C=CC=CC=1>>[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C@H:38]3[C@@:40]4([C:48]5[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=5)[N:42]([CH3:49])[C:41]4=[O:50])[CH2:39]3)[CH:36]=2)[CH:31]=[N:30]1

Participants

3

Reactant 2

HCID 58486234(1R,2S)-2-(1-benzyl-1H-indazol-6-yl)-1'-methylspiro[cyclopropane-1,3'-indolin]-2'-oneHCID 58486367(1R*,2S*)-2-(1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58486176(1R,2S)-2-(1H-indazol-6-yl)-1'-methylspiro[cyclopropane-1,3'-indolin]-2'-oneYield 74.1%

Procedure

Method 1 (Bn): The title compound was prepared in a manner similar to the method of (1R,2S)-2-(1H-indazol-6-yl)spiro[cyclopropane-1,3′-indolin]-2′-one using (1R,2S)-2-(1-benzyl-1H-indazol-6-yl)-1′-methylspiro[cyclopropane-1,3′-indolin]-2′-one (1.16 g, 3.06 mmol). Purification via column chromatography (silica gel, 3-6% MeOH in CH2Cl2) yielded the title compound as a pale-yellow solid (656 mg, 74%); 1H NMR (400 MHz, CDCl3) δ 10.06 (br. s, 1H), 8.05 (s, 1H), 7.64 (d, 1H, J=7.6 Hz), 7.36 (s, 1H), 7.14 (t, J=8.7 Hz, 1H), 6.97 (d, J=8.7 Hz, 1H), 6.87 (d, J=8.2 Hz, 1H), 6.62 (t, J=7.6 Hz, 1H), 5.91 (d, J=7.9 Hz, 1H), 3.46 (t, J=7.8 Hz, 1H), 3.34 (s, 3H), 2.26-2.23 (m, 1H), 2.08-2.04 (m, 1H); MS ESI 290.1 [M+H]+, calcd for [C18H15N3O+H]+ 290.13.

Workup

  1. customPurification via column chromatography (silica gel, 3-6% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c892d039d93b4d939bc4e7ecacc6644b
Source dataset
uspto-grants-2014_12
Patent number
US08921545B2

Reaction notes

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