Triethylamine → HCID 68488148, compound

HRID 1401464Notes

Reaction equation

HRID 1401464 reaction equation
[CH2:1]([N:4]1[C:12]2[CH:11]=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=2[C:6]2[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C:5]1=2)[CH:2]=[CH2:3].[F:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:3]=[CH:2][CH2:1][N:4]2[C:12]3[CH:11]=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=3[C:6]3[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C:5]2=3)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99931-Bromo-4-fluorobenzeneHCID 11776TriphenylphosphineHCID 67309984HCID 67309984, compound

Product 1

HCID 68488148HCID 68488148, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

5-Allyl-8-chloro-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole (200 mg, 0.76 mmol, 1 equiv.) and 4-fluorobromobenzene (134 mg, 0.76 mmol, 1 equiv.) were heated to 100° C. with palladium acetate (5 mg, 0.023 mmol), triphenyl phosphine (12 mg, 0.046 mmol) and triethyl amine (0.22 mL, 2 equiv.) in THF (5 mL) for 14 h. The reaction mixture was cooled to RT and diluted with THF (10 mL), filtered over a Celite bed and concentrated. The concentrate was dissolved in EtOAc (20 mL) and washed with water (5 mL) followed by brine. The organic layer was dried over anhydrous sodium sulfate, and evaporated under reduced pressure to obtain crude product that was purified by HPLC. 1H NMR (DMSO-d6) δ (ppm): 10.0 (bs, 1H), 7.61-7.58 (d, 2H), 7.44-7.40 (dd, 2H), 7.20-7.11 (m, 3H), 6.4 (d, 1H), 6.3 (m, 1H), 5.0 (m, 2H), 4.62 (d, 1H), 4.29-4.25 (m, 1H), 3.78 (m, 1H), 3.5 (m, 1H), 3.18 (m, 2H), 2.98 (s, 3H).

Workup

  1. filtrationfiltered over a Celite bed
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in EtOAc (20 mL)
  4. washwashed with water (5 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customto obtain crude product that
  8. customwas purified by HPLC

Sources & evidence

ORD record
ord-a327ce0303784205825840d8abff83a2
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

Loading…