Potassium Phosphate, Tribasic → HCID 59455197, compound

HRID 1401553Notes

Reaction equation

HRID 1401553 reaction equation
[CH:1]([N:4]1[CH2:17][CH2:16][C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1)([CH3:3])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.Br[CH:35]=[C:36]([C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1)[CH3:37]>CN(C=O)C.[Cu]I>[CH:1]([N:4]1[CH2:17][CH2:16][C:7]2[N:8](/[CH:35]=[C:36](/[C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)\[CH3:37])[C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 904939HCID 904939, compoundHCID 86642478(E)-4-(1-bromoprop-1-en-2-yl)pyridine

Product 1

HCID 59455197HCID 59455197, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

2-Isopropyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (114 mg, 0.5 mmol), potassium phosphate (212 mg, 1 mmol), copper (I) iodide (9.5 mg, 0.05 mmol) and L-proline (11.5 mg, 0.1 mmol) were mixed in DMF and the contents were purged with nitrogen. 4-(1-Bromoprop-1-en-2-yl)pyridine (107.83 mg, 0.55 mmol) was added, the reaction mixture was purged with nitrogen and heated overnight at 140° C. The contents were purged with nitrogen and heated overnight at 140° C. The contents were cooled to RT and poured into water. The precipitate obtained was filtered, dried and purified by silica gel chromatography (100-200 mesh, neutralized with aqueous ammonia) eluting with 0-4% MeOH-DCM as eluent. The compound was further purified by HPLC. 1H NMR (DMSO-d6, oxalate salt) δ (ppm): 8.60 (d, 2H), 7.70 (d, 2H), 7.45 (s, 1H), 7.40 (s, 1H), 7.18 (d, 1H), 7.05 (d, 1H), 4.50 (m, 2H), 3.80 (m, 3H), 3.10 (m, 2H), 2.42 (s, 3H), 2.00 (s, 3H), 1.40 (d, 6H).

Workup

  1. customthe contents were purged with nitrogen
  2. customthe reaction mixture was purged with nitrogen
  3. customThe contents were purged with nitrogen
  4. temperatureheated overnight at 140° C
  5. temperatureThe contents were cooled to RT
  6. additionpoured into water
  7. customThe precipitate obtained
  8. filtrationwas filtered
  9. customdried
  10. custompurified by silica gel chromatography (100-200 mesh, neutralized with aqueous ammonia)
  11. washeluting with 0-4% MeOH-DCM as eluent
  12. customThe compound was further purified by HPLC

Sources & evidence

ORD record
ord-ea2c775648564313af3b509e4ba13916
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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