Potassium Phosphate, Tribasic → HCID 86644774, compound

HRID 1401660Notes

Reaction equation

BrC=C([C:5]1[CH:6]=[C:7]([F:14])[C:8]([O:12]C)=[C:9]([F:11])[CH:10]=1)C.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>[CH3:31][N:32]1[CH2:45][CH2:44][C:35]2[N:36]([C:8]3([OH:12])[C:9]([F:11])=[CH:10][CH:5]=[CH:6][CH:7]3[F:14])[C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][C:42]=3[C:34]=2[CH2:33]1

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: 52 mg. 1H NMR (CD3OD, HCl salt) δ (ppm): 7.30 (s, 1H), 7.24 (d, 2H), 7.10 (m, 2H), 7.0 (s, 1H), 4.70 (m, 1H), 4.40 (m, 1H), 3.82 (m, 1H), 3.60 (m, 1H), 3.18 (s, 3H), 3.14 (m, 2H), 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-794fe393094949479fa93c1c21e9486c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

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