Toluene → HCID 58110604, compound

HRID 2096997Notes

Reaction equation

HRID 2096997 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:10][C:3]=12.[CH3:19][C:20]1[N:21]=[CH:22][N:23]([C:25]2[CH:30]=[CH:29][C:28]([Sn](CCCC)(CCCC)CCCC)=[CH:27][CH:26]=2)[CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([C:28]4[CH:29]=[CH:30][C:25]([N:23]5[CH:24]=[C:20]([CH3:19])[N:21]=[CH:22]5)=[CH:26][CH:27]=4)=[C:3]3[CH:10]=[CH:9]2)=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 58110626HCID 58110626, compoundHCID 58110670HCID 58110670, compound

Product 1

HCID 58110604HCID 58110604, compoundYield 10.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 4-chloro-1-(4-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine (36 mg, 0.14 mmol), 4-methyl-1-(4-(tributylstannyl)phenyl)-1H-imidazole (100 mg, 0.21 mmol) and Potassium carbonate (100 mg, 0.7 mmol) was added 3 ml Toluene followed by Pd(PPh3)4 (20 mg, 0.014 mmol) then heat to 120 C for 2 hrs. The reaction was worked up by cooling to RT then adding water and DCM. Extract aqueous layer 3×DCM, then dry over sodium sulfate and filter and concentrate to dryess. The residue was purified by chromatography over silica gel (eluted with DCM/MeOH 99:1 to 90:10) to provide 5.8 mg (10%) of product. 1H NMR (CDCl3 400 MHz): 8.4 (d, 1H), 8.01 (s, 2H), 7.78-7.8 (m, 1H), 7.4 (s, 2H), 7.26-7.27 (m, 3H), 6.95-7.02 (m, 3H), 6.65-6.72 (m, 1H), 5.53 (s, 1H), 3.93 (s, 3H), 2.33 (s, 3H). LCMS (MH+)=413; retention time=3.19 min.

Workup

  1. temperaturethen heat to 120 C for 2 hrs
  2. dry with materialExtract aqueous layer 3×DCM, then dry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customThe residue was purified by chromatography over silica gel (eluted with DCM/MeOH 99:1 to 90:10)

Sources & evidence

ORD record
ord-6f24e8ec46d54d8e9e7f2e7c06585ddf
Source dataset
uspto-grants-2013_05
Patent number
US08450343B2

Reaction notes

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