Cesium carbonate → HCID 44518227, compound

HRID 1890668Notes

Reaction equation

HRID 1890668 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:42]1[N:47]=[C:46]2[N:48]([C:51]3[CH:52]=[C:53]([CH:56]=[CH:57][CH:58]=3)[C:54]#[N:55])[CH:49]=[N:50][C:45]2=[CH:44][CH:43]=1.[F:59][C:60]1[CH:61]=[C:62]([CH:66]2[CH2:70][CH2:69][CH2:68][NH:67]2)[CH:63]=[CH:64][CH:65]=1>O1CCOCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[F:59][C:60]1[CH:61]=[C:62]([CH:66]2[CH2:70][CH2:69][CH2:68][N:67]2[C:42]2[N:47]=[C:46]3[N:48]([C:51]4[CH:52]=[C:53]([CH:56]=[CH:57][CH:58]=4)[C:54]#[N:55])[CH:49]=[N:50][C:45]3=[CH:44][CH:43]=2)[CH:63]=[CH:64][CH:65]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 39124022-(3-Fluorophenyl)pyrrolidineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 58335594HCID 58335594, compound

Product 1

HCID 44518227HCID 44518227, compound

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In step 1-4, tris(dibenzylideneacetone) dipalladium (0) (10.8 mg, 0.012 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (22 mg, 0.047 mmol) and cesium carbonate (77 mg, 0.24 mmol) were added consecutively into a solution of 3-(5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)benzonitrile (30 mg, 0.12 mmol) and 2-(3-fluorophenyl)pyrrolidine (29 mg, 0.18 mmol) in 1,4-dioxane. The mixture was degased under house vacuum, and charged with nitrogen and heated for 18 hours at 100° C. The reaction mixtures was purified using HPLC to afford 3-(5-(2-(3-fluorophenyl)pyrrolidin-1-yl)-3H-imidazo[4,5-b]pyridin-3-yl)benzonitrile (1-4) as a white solid. 1H NMR methanol-d4 δ (ppm) 8.86 (s, 1H), 8.28 (s, 1H), 7.98 (m, 1H), 7.89 (d, 1H), 7.78 (d, 1H), 7.63 (t, 1H), 7.33 (m, 1H), 7.09 (dm, 1H), 6.93 (m, 2H), 6.70 (d, 1H), 5.18 (d, 1H), 3.94 (m, 1H), 3.68 (m, 1H), 2.48 (m, 1H), 2.11 (m, 2), 1.97 (m, 1H); m/z 384 (M+1).

Workup

  1. customThe mixture was degased under house vacuum
  2. additioncharged with nitrogen
  3. customThe reaction mixtures
  4. customwas purified

Sources & evidence

ORD record
ord-bd5a574a51694c1a8bcc8231fcdffea6
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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