Sodium Carbonate → 3-(1-Boc-2-(s)-azetidinylmethoxy)-5-(2-thienyl)pyridine

HRID 365874Notes

Reaction equation

[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18](Br)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1B(O)O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([C:28]2[S:27][CH:31]=[CH:30][CH:29]=2)[CH:19]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 3-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromopyridine (0.42 g, 1.2 mmol), tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.034 mmol), sodium carbonate (2.0 M, 2 mL) in toluene (10 mL) was added 2-thienylboronic acid (0.38 g, 3.0 mmol). The reaction mixture was stirred and heated at 80° C. for 16 h. Solvent was evaporated. The residue was chromatographed (silica gel; hexane/EtOAC, 10:1 to 2:1) to afford an oil (0.24 g, 57%): 1H NMR (CDCl3, 300 MHz) δ1.42 (s, 9H), 2.26-2.90 (m, 2H), 3.86-3.94 (m, 2H), 4.20 (m, 1H), 4.39 (m, 1H), 4.55 (m, 1H), 7.12 (m, 1H), 7.36 (s, 1H), 7.44 (s, 1H), 8.26 (s, 1H), 8.50 (s, 1H); MS (CI/NH3) m/z 347 (M+H)+.

Workup

customSolvent was evaporated
customThe residue was chromatographed (silica gel; hexane/EtOAC, 10:1 to 2:1)

Sources & evidence

ORD record: ord-ec0839a3f68b49f19833a3ed87daf309
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127386

Reaction notes

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