Potassium Phosphate, Tribasic → HCID 59455091, compound

HRID 1401666Notes

Reaction equation

Br[CH:2]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)[CH3:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.[CH3:29][N:30]1[CH2:43][CH2:42][C:33]2[NH:34][C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][C:40]=3[C:32]=2[CH2:31]1>CN(C=O)C.[Cu]I>[CH3:29][N:30]1[CH2:43][CH2:42][C:33]2[N:34](/[CH:2]=[C:3](/[C:5]3[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=3)\[CH3:4])[C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][C:40]=3[C:32]=2[CH2:31]1

Participants

Conditions

Temperature: 85 °C

Procedure

(4-(1-Bromoprop-1-en-2-yl)phenyl)(methyl)sulfane (241 mg, 1 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 compound was purified on silica gel (100-200 mesh) using 0-3% MeOH:DCM as eluent. Yield: 72 mg. 1H NMR (CD3OD, oxalate salt) δ (ppm): 7.59 (d, 2H), 7.30 (m, 3H), 7.10 (m, 2H), 7.0 (s, 1H), 4.60 (m, 2H), 3.70 (m, 2H), 3.28 (m, 2H), 3.10 (s, 3H), 2.54 (s, 3H), 2.42 (s, 3H), 1.96 (s, 3H).

Workup

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

Sources & evidence

ORD record: ord-b0202bd1c3084d31ac7b51eea4464173
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

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