Dichloromethane → HCID 59700026, compound

HRID 901502Notes

Reaction equation

HRID 901502 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.I[C:38]1[CH:39]=[C:40]([C:44]2[NH:45][CH2:46][CH2:47][N:48]=2)[CH:41]=[CH:42][CH:43]=1.ClCCl.C(=O)(O)[O-:53].[Na+]>C(#N)C>[NH:48]1[CH2:47][CH2:46][N:45]=[C:44]1[C:40]1[CH:39]=[C:38]([C:15]2[CH:16]=[C:17]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[CH:10][NH:11][C:12]3=[N:13][CH:14]=2)[CH:43]=[CH:42][CH:41]=1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:38]3[CH:39]=[C:40]([C:44]4([OH:53])[NH:45][CH2:46][CH2:47][NH:48]4)[CH:41]=[CH:42][CH:43]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 67061232HCID 67061232, compound

Product 2

HCID 59700026HCID 59700026, compoundHCID 59700038HCID 59700038, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the 3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (43 mg, 0.085 mmol), 2-(3-Iodo-phenyl)-4,5-dihydro-1H-imidazole (34.7 mg, 0.128 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (3.1 mg, 4.2 μmol) in 0.8 ml acetonitrile/0.8 ml 2N sodium carbonate irradiated in a Personal Chemistry Optimizer at 135° C. for 20 minutes. The crude reaction mixture was distributed between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The aqueous phase was then extracted with dichloromethane and the combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude product was then purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 5-[3-(4,5-Dihydro-1H-imidazol-2-yl)-phenyl]-3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine (11.2 mg, MS: MS: m/z 369.1 [MH+]) and 2-{3-[3-(2-Methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-imidazolidin-2-ol (13.2 mg, m/z 387.1 [MH+]), both as green solid.

Workup

  1. customirradiated in a Personal Chemistry Optimizer at 135° C. for 20 minutes
  2. customThe crude reaction mixture
  3. extractionThe aqueous phase was then extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was then purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-d79fe67d06e34a1fbeb6071509e4191f
Source dataset
uspto-grants-2008_04
Patent number
US07361764B2

Reaction notes

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