Cesium carbonate → HCID 58335772, compound

HRID 1890692Notes

Reaction equation

HRID 1890692 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH:20]=[CH:21][N:22]=2)[CH:19]=1.Br[C:24]1[CH:25]=[CH:26][C:27]([F:32])=[C:28]([CH:31]=1)[C:29]#[N:30].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([C:24]3[CH:25]=[CH:26][C:27]([F:32])=[C:28]([CH:31]=3)[C:29]#[N:30])=[CH:21][N:22]=2)[CH:19]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27249005-Bromo-2-fluorobenzonitrileHCID 58335807HCID 58335807, compound

Product 1

HCID 58335772HCID 58335772, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

In step 13-3, a sealed vial was charged with 6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine (30 mg, 0.1 mmol), 5-bromo-2-fluorobenzonitrile (20 mg, 0.1 mmol), Pd(OAc)2 (1 mg, 0.005 mmol), Xantphos (6 mg, 0.01 mmol), Cs2CO3 (49 mg, 0.15 mmol), Bu4NHSO4 (3 mg, 0.01 mmol) and 1,4-dioxane (0.5 ml), and the mixture was heated to 90° C. overnight. The mixture was filtered through celite. The filtrate was concentrated and purified by preparative LC-MS to give 5-(6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridin-3-yl)-2-fluorobenzonitrile (12-3). LC-MS: 419.2 (MH+).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by preparative LC-MS

Sources & evidence

ORD record
ord-7a7cf69d054e49099a6f041470658a83
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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