Potassium Carbonate → HCID 22220424, compound

HRID 1061228Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1F)[CH:15]=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN1CCCN(C)C1=O.C(#N)C>[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[N:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[CH:15]=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,4-dioxa-8-azaspiro[4.5]decane (6.87 g, 48 mmol), 3-bromo-4-fluorobenzaldehyde (8.12 g, 40 mmol), and potassium carbonate (6.63 g, 48 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (12 mL) and acetonitrile (8 mL) was heated at 80° C. under N2 atmosphere for one day. Reaction mixture was cooled down to room temperature and poured onto water (150 mL). The mixture was extracted with methylene chloride. The organic layer was dried (MgSO4) and concentrated to give the title compound as an off-white solid (12.4 g, 96%); mp 63-64° C.; 1H NMR (300 MHz, CDCl3) δ 1.93 (t, J=5.7 Hz, 4H), 3.25 (t, J=5.4 Hz, 4H), 4.02 (s, 4H), 7.12 (d, J=4.2 Hz, 1H), 7.75 (dd, J=8.4, 2.1 Hz, 2H), 8.06 (d, J=1.8 Hz, 1H), 9.84 (s, 1H); MS (ES) m/z: 325.7 (MH+); HRMS Calcd. for C14H16BrNO3 (MH+): 325.0314. Found: 325.0288.

Workup

customReaction mixture
temperaturewas cooled down to room temperature
additionpoured onto water (150 mL)
extractionThe mixture was extracted with methylene chloride
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-502a2b5d3adb4f68a8c5f44c730e54e6
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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