Potassium Phosphate, Tribasic → HCID 59455102, compound

HRID 1401634Notes

Reaction equation

HRID 1401634 reaction equation
Br[C:2]([CH3:12])=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[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>[F:11][C:8]1[CH:9]=[CH:10][C:5](/[C:3](/[CH3:4])=[C:2](/[N:34]2[C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][C:40]=3[C:32]3[CH2:31][N:30]([CH3:29])[CH2:43][CH2:42][C:33]2=3)\[CH3:12])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 86644770HCID 86644770, compound

Product 1

HCID 59455102HCID 59455102, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

1-(3-Bromobut-2-en-2-yl)-4-fluorobenzene (250 mg, 1.2 mmol) was dissolved in DMF (5 mL). 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 nitrogen gas was purged into the reaction mixture for 2 min. The contents were stirred at 85° C. overnight. Water (5 mL) was added and the solid mass was filtered under vacuum to obtain crude compound which was purified on silica gel (100-200 mesh) using 0-3% MeOH: DCM as eluent. The compound was further purified through reverse phase chromatography. Yield: 6 mg. 1H NMR (CD3OD, HCl salt) δ (ppm): 7.42 (m, 2H), 7.30 (s, 1H), 7.20 (m, 3H), 7.10 (d, 1H), 4.70 (d, 1H), 4.40 (d, 1H), 3.90 (m, 1H), 3.62 (m, 1H), 3.25 (m, 1H), 3.16 (s, 3H), 3.10 (m, 1H), 2.42 (s, 3H), 1.94 (d, 3H), 1.64 (d, 3H).

Workup

  1. customnitrogen gas was purged into the reaction mixture for 2 min
  2. additionWater (5 mL) was added
  3. filtrationthe solid mass was filtered under vacuum
  4. customto obtain crude compound which
  5. customwas purified on silica gel (100-200 mesh)
  6. customThe compound was further purified through reverse phase chromatography

Sources & evidence

ORD record
ord-5b7534825c694706a047234b53425de0
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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