3-Bromopyridine → HCID 66757914, compound

HRID 393781Notes

Reaction equation

HRID 393781 reaction equation
[CH2:1]([N:8]1[CH2:14][C@@H:13]2[C@H:9]1[CH2:10][CH2:11][NH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.CC(C)([O-])C.[Na+]>>[CH2:1]([N:8]1[CH2:14][C@@H:13]2[C@H:9]1[CH2:10][CH2:11][N:12]2[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 122863-BromopyridineHCID 23676156Sodium t-butoxideHCID 66757773HCID 66757773, compound

Product 1

HCID 66757914HCID 66757914, compoundYield 98%

Procedure

The product from Example 18E (260 mg, 1.0 mmol) and 3-bromopyridine were processed as described in Example 1E, except that a larger amount of sodium tert-butoxide (384 mg, 4.0 mmol) was used to neutralize the salt. The crude product was purified by chromatography (SiO2, CH2Cl2:MeOH, 95:5, Rf 0.3) to provide the title compound (0.26 g, 98% yield). 1H NMR (CD3OD, 300 MHz) δ2.40 (m, 2H), 3.20 (m, 2H), 3.50-3.80 (m, 4H), 4.10 (m, 1H), 4.50 (m, 1H), 7.00-7.60 (m, 9H); MS (DCI/NH3) m/z 266 (M+H)+.

Workup

  1. customThe crude product was purified by chromatography (SiO2, CH2Cl2:MeOH, 95:5, Rf 0.3)

Sources & evidence

ORD record
ord-bc6f5855654e4cca8cbb0c36ccabda8c
Source dataset
uspto-grants-2004_10
Patent number
US06809105B2

Reaction notes

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