1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl acetate → 1-(4-(6-((1R*,2S*)-5'-methoxy-2'-oxospiro[cyclopropane-1,3'-indoline]-2-yl)-1H-indazol-3-yl)phenyl)piperidin-4-yl acetate

HRID 2383689Notes

Reaction equation

HRID 2383689 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C@H:11]3[C@@:13]4([C:21]5[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=5)[NH:15][C:14]4=[O:24])[CH2:12]3)=[CH:8][CH:9]=2)[NH:4][N:3]=1.[C:25]([O:28][CH:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)(=[O:27])[CH3:26]>>[C:25]([O:28][CH:29]1[CH2:30][CH2:31][N:32]([C:35]2[CH:40]=[CH:39][C:38]([C:2]3[C:10]4[C:5](=[CH:6][C:7]([C@H:11]5[C@@:13]6([C:21]7[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=7)[NH:15][C:14]6=[O:24])[CH2:12]5)=[CH:8][CH:9]=4)[NH:4][N:3]=3)=[CH:37][CH:36]=2)[CH2:33][CH2:34]1)(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 667303481-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl acetateHCID 178487035HCID 178487035, compound

Product 1

HCID 674484371-(4-(6-((1R*,2S*)-5'-methoxy-2'-oxospiro[cyclopropane-1,3'-indoline]-2-yl)-1H-indazol-3-yl)phenyl)piperidin-4-yl acetateYield 41%

Procedure

The title compound was synthesized according to the method described for example A45 except reacting a (1R*,2S*)-2-(3-iodo-1H-indazol-6-yl)-5′-methoxyspiro[cyclopropane-1,3′-indolin]-2′-one (76 mg, 0.18 mmol) with 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl acetate (67 mg, 0.19 mmol). Crude product was purified by flash chromatography using EtOAc/Hexanes (2:3 to 1:0) to give the title compound as a yellow solid (38 mg, 41%). MS ESI 523.3[M+H]+, calcd for [C31H30N4O4+H]+ 523.23.

Workup

  1. customThe title compound was synthesized
  2. customCrude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ece32285029649f5935da150dbb49b53
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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