2-Bromopyridine → HCID 66598387, compound

HRID 334808Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:17](=[O:22])[CH2:18][CH2:19][C:20]#[CH:21])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:17](=[O:22])[CH2:18][CH2:19][C:20]#[C:21][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]

Participants

Reactant 2

HCID 79732-Bromopyridine

HCID 86630256HCID 86630256, compound

Product 1

HCID 66598387HCID 66598387, compoundYield 61%

Procedure

The title compound was prepared in accordance with the general method of Example 244(C), from tert-butyl 2,4-difluorophenyl(pent-4-ynoyl)carbamate (250 mg, 0.82 mmol) and 2-bromopyridine (129 mg, 0.82 mmol). The crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column cyclohexane/AcOEt: 70/30 as eluent) to afford 193 mg of tert-butyl 2,4-difluorophenyl(5-(pyridin-2-yl)pent-4-ynoyl)carbamate as a brown oil (Yield: 61%).

Workup

customThe crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column cyclohexane/AcOEt: 70/30 as eluent)

Sources & evidence

ORD record: ord-6587a91a91d445f5b781ba21ffd0f647
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883826B2

Reaction notes

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