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Bromocycloheptane → methyl 3-(1-cycloheptyl-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanoate

HRID 218169
Notes
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Reaction equation

HRID 218169 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH:35]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>CS(C)=O>[CH:35]1([N:1]2[C:9]3[C:4](=[CH:5][C:6]([CH:10]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=3)[CH:3]=[N:2]2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 16992BromocycloheptaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 59251051methyl 3-(1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanoate

Product 1

HCID 68702551methyl 3-(1-cycloheptyl-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanoateYield 60%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
85 °C

Procedure

Methyl 3-(1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanoate (500 mg, 1.62 mmol, prepared in Synthetic Intermediate III(c)) was dissolved in 5 mL DMSO and NaHMDS (2.4 mL, 2.4 mmol, 1.0 M in THF) was added followed by bromocycloheptane (446 uL, 3.25 mmol). The reaction was heated overnight at 85° C. The reaction was quenched with TFA and purified by HPLC to give methyl 3-(1-cycloheptyl-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanoate (393 mg, 60%). (M+H)+=405.

Workup

  1. customThe reaction was quenched with TFA
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-60fecc13f5284888bf25953c32ff45cc
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08198311B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes