3-Bromopyridine → HCID 66758375, compound

HRID 393787Notes

Reaction equation

CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([N:19]1[C@@H:26]2[C@@H:21]([CH2:22][CH2:23][NH:24][CH2:25]2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Br[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1.CC(C)([O-])C.[Na+]>>[CH2:12]([N:19]1[C@@H:26]2[C@@H:21]([CH2:22][CH2:23][N:24]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[CH2:25]2)[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Reactant 3

HCID 122863-Bromopyridine

HCID 23676156Sodium t-butoxide

HCID 86584377HCID 86584377, compound

Product 1

HCID 66758375HCID 66758375, compoundYield 57%

Procedure

The product from Example 33E and 3-bromopyridine were processed according to the procedure of Example 1E, except that a larger amount of sodium tert-butoxide (384 mg, 4.0 mmol) was used. The residue was purified by chromatography (SiO2, hexanes: ethyl acetate, 20:80, Rf. 0.2) to provide the title compound (0.16 g, 57% yield). 1H NMR (CD3OD, 300 MHz) δ2.04 (m, 2H), 2.56 (m, 1H), 3.00 (m, 2H), 3.22 (m, 2H), 3.55 (m, 1H), 3.60 (d, J=12.5 Hz, 1H), 3.70 (d, J=12.5 Hz, 1H), 3.55 (m, 1H), 3.70 (m, 1H), 7.04 (ddd, J=8.8, 3.0, 1.3 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 7.24 (m, 5H), 7.80 (dd, J=4.7, 1.3 Hz, 1H), 7.84 (d, J=3.0 Hz, 1H); MS (DCI/NH3) m/z 280 (M+H)+.

Workup

customThe residue was purified by chromatography (SiO2, hexanes: ethyl acetate, 20:80, Rf. 0.2)

Sources & evidence

ORD record: ord-3f4ae02cba99454c98106057b35d6158
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809105B2

Reaction notes

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