(1R,2S)-1'-benzyl-2-(1-benzyl-1H-indazol-6-yl)-5'-fluorospiro[cyclopropane-1,3'-indolin]-2'-one → (1R,2S)-5'-fluoro-2-(1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one

HRID 1410352Notes

Reaction equation

HRID 1410352 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][C:34]([F:38])=[CH:35][CH:36]=2)[C@:31]2([CH2:40][C@H:39]2[C:41]2[CH:49]=[C:48]3[C:44]([CH:45]=[N:46][N:47]3CC3C=CC=CC=3)=[CH:43][CH:42]=2)[C:30]1=[O:57])C1C=CC=CC=1>>[F:38][C:34]1[CH:33]=[C:32]2[C:37](=[CH:36][CH:35]=1)[NH:29][C:30](=[O:57])[C@:31]12[CH2:40][C@H:39]1[C:41]1[CH:49]=[C:48]2[C:44]([CH:45]=[N:46][NH:47]2)=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 58486133(1R,2S)-1'-benzyl-2-(1-benzyl-1H-indazol-6-yl)-5'-fluorospiro[cyclopropane-1,3'-indolin]-2'-oneHCID 58486367(1R*,2S*)-2-(1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58486165(1R,2S)-5'-fluoro-2-(1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-oneYield 52%

Procedure

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)-1′-benzyl-2-(1-benzyl-1H-indazol-6-yl)-5′-fluorospiro[cyclopropane-1,3′-indolin]-2′-one (560 mg, 1.18 mmol). Purification by using silica gel column chromatography with 5-95% EtOAc in hexane to give the title compound as a creamy solid (179 mg, 52%). NMR (400 MHz, CD3OD) δ 8.03 (s, 1H), 7.71 (d, J=8.0 Hz, 1H), 7.62-7.46 (m, 2H), 6.94 (d, J=8.4 Hz, 1H), 6.88 (t, J=4.8 Hz, 1H), 5.69 (d, J=9.2 Hz, 1H), 3.39 (t, J=8.0 Hz, 1H), 2.30-2.71 (m, 1H), 2.23-2.18 (m, 1H); MS ESI 294.1 [M+H]+, calcd for [C17H12FN3O+H]+ 294.10.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-6fb545cd7a1d4197b762dd964c391a13
Source dataset
uspto-grants-2014_12
Patent number
US08921545B2

Reaction notes

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