2-Bromopyridine → HCID 67367584, compound

HRID 1753160Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[N:13]1([CH2:18][C:19](OCC)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14]1.[NH4+].[Cl-]>C1COCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:19](=[O:20])[CH2:18][N:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-bromopyridine (380 μL, 4.0 mmol) in dry THF (15 mL) was added n-BuLi (1.6 M in hexanes, 2.5 mL, 4.0 mmol) at −78° C. The dark brown mixture was stirred for 30 minutes before a solution of ethyl 1H-pyrrol-1-ylacetate (720 mg, 4.7 mmol) in THF (5 mL) was added. The brown solution was stirred at −78° C. for 40 minutes and then at room temperature for 2 hours. The solution was poured into a saturated aqueous solution of NH4Cl (30 mL) and extracted with EtOAc (3×20 mL). The organic layers were dried (MgSO4), filtered and concentrated in vacuo to give a dark yellow oil that was purified by flash chromatography (Biotage SP4, 40 g cartridge, gradient 0-60% EtOAc in hexanes). To give 1-(Pyridine-2-yl)-2-(1H-pyrrol-1-yl)ethanone as a oil (470 mg, yield 63%). 1H-NMR (400 MHz, CDCl3): δ 5.60 (s, 2H), 6.23-6.27 (m, 2H), 6.69-6.72 (m, 2H), 7.54 (ddd, 1H, J 7.5, 4.8, 1.1 Hz), 7.88 (dt, 1H, J 7.7, 1.7 Hz), 8.06-8.10 (m, 1H), 8.69-8.73 (m, 1H).

Workup

additionwas added
waitat room temperature for 2 hours
extractionextracted with EtOAc (3×20 mL)
dry with materialThe organic layers were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto give a dark yellow oil that
customwas purified by flash chromatography (Biotage SP4, 40 g cartridge, gradient 0-60% EtOAc in hexanes)

Sources & evidence

ORD record: ord-fa006c295de14de7ab7cd055534d8429
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163029B2

Reaction notes

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