Potassium Phosphate, Tribasic → HCID 59455017, compound

HRID 1401663Notes

Reaction equation

Br[CH:2]=[C:3]([C:5]1[CH:6]=[C:7]([F:14])[C:8]([O:12][CH3:13])=[C:9]([F:11])[CH:10]=1)[CH3:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.[CH3:31][N:32]1[CH2:45][CH2:44][C:35]2[NH:36][C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][C:42]=3[C:34]=2[CH2:33]1>CN(C=O)C.[Cu]I>[F:11][C:9]1[CH:10]=[C:5](/[C:3](/[CH3:4])=[CH:2]/[N:36]2[C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][C:42]=3[C:34]3[CH2:33][N:32]([CH3:31])[CH2:45][CH2:44][C:35]2=3)[CH:6]=[C:7]([F:14])[C:8]=1[O:12][CH3:13]

Participants

Conditions

Temperature: 85 °C

Procedure

5-(1-Bromoprop-1-en-2-yl)-1,3-difluoro-2-methoxybenzene (223 mg, 1.2 mmol) was dissolved in DMF (5 mL) and potassium phosphate (424 mg, 2 mmol) was added followed by copper (I) iodide (19 mg, 0.1 mmol) and L-proline (23 mg, 0.2 mmol). 2,3,4,5-Tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (200 mg, 1 mmol) was added and the mixture purged with nitrogen for 2 min. The reaction mixture was stirred at 85° C. overnight. Water was added and the solid mass was filtered under vacuum. The crude product was purified on silica gel (100-200 mesh) using 0-10% MeOH:DCM as eluent. Yield: 63 mg. 1H NMR (CD3OD, HCl salt) δ (ppm): 7.32 (s, 1H), 7.30 (s, 2H), 7.08 (m, 3H), 4.72 (m, 1H), 4.39 (m, 1H), 4.0 (s, 3H), 3.82 (m, 1H), 3.60 (m, 1H), 3.20-3.10 (m, 5H), 2.42 (s, 3H), 1.90 (s, 3H).

Workup

customthe mixture purged with nitrogen for 2 min
additionWater was added
filtrationthe solid mass was filtered under vacuum
customThe crude product was purified on silica gel (100-200 mesh)

Sources & evidence

ORD record: ord-64dbcf1720aa4879a0841d2129d115d8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

Loading…