2,6-Dibromopyridine → 9-(6-Bromopyridin-2-yl)-3-azaspiro[5.5]undec-8-ene

HRID 419280Notes

Reaction equation

[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[N:8]=1.C(OC([N:21]1[CH2:26][CH2:25][C:24]2([CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]2)[CH2:23][CH2:22]1)=O)(C)(C)C>ClCCl>[Br:13][C:9]1[N:8]=[C:7]([C:29]2[CH2:30][CH2:31][C:24]3([CH2:25][CH2:26][NH:21][CH2:22][CH2:23]3)[CH2:27][CH:28]=2)[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Was prepared according to method A with the following variation: n-BuLi (1.6 M in hexanes (1.93 mL, 4.82 mmol)) was added drop-wise to a solution of 2,6-dibromopyridine (1.06 g, 4.48 mmol) in dichloromethane (25 mL). The reaction was stirred −78° C. for 30 min. 9-Oxo-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (300 mg, 1.12 mmol) in dichloromethane (5 mL) was added drop-wise and the mixture was stirred at −78° C. for 1 h. White solid. Mp. 161.3-162.8° C.

Workup

customWas prepared
stirringthe mixture was stirred at −78° C. for 1 h

Sources & evidence

ORD record: ord-ddc3ebe233a642649bd7903e5dc13537
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093388B2

Reaction notes

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