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

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

Participants

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

customThe reaction was quenched with TFA
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

Linked notes

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