(2-Bromo-Pyridin-3-Yl)-Carbamic Acid Tert-Butyl Ester → Tert-butyl 2-(hydroxy(1-(3-(trifluoromethyl)phenyl)cyclobutyl)methyl)-pyridin-3-ylcarbamate

HRID 1620996Notes

Reaction equation

Br[C:2]1[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([C:29]2([CH:33]=[O:34])[CH2:32][CH2:31][CH2:30]2)[CH:26]=[CH:27][CH:28]=1>C1COCC1>[OH:34][CH:33]([C:29]1([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:35])[F:36])[CH:24]=2)[CH2:30][CH2:31][CH2:32]1)[C:2]1[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of Example 120A (400 mg, 1.465 mmol) in THF (5 mL) was added n-BuLi (3.08 mmol) at −78° C. The resulting solution was stirred at about −78° C. for about 1 hour and then a solution of Example 120C (365 mg, 1.611 mmol) in 10 mL of THF was added. The temperature was warmed to room temperature, stirred for another 1 hour, quenched with 10 mL of water, and extracted with ethyl acetate. The organic layer was washed with brine, and the combined organic phases were dried over sodium sulfate, filtered, and concentrated to give the desired crude product, which was used for next step without further purification. LC-MS: m/z (M+H) 439.

Workup

temperatureThe temperature was warmed to room temperature
stirringstirred for another 1 hour
customquenched with 10 mL of water
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialthe combined organic phases were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-4e1f97c4296c4a69bf136b31f4d6e16d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772500B2

Reaction notes

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