Cesium carbonate → HCID 59331184, compound

HRID 2088323Notes

Reaction equation

HRID 2088323 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.I[C:15]1[CH:31]=[CH:30][C:18]([C:19]([NH:21][C@H:22]2[CH:27]3[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]3)[CH2:23]2)=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.O>[N:24]12[CH2:29][CH2:28][CH:27]([CH2:26][CH2:25]1)[C@H:22]([NH:21][C:19]([C:18]1[CH:30]=[CH:31][C:15]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=3)=[CH:16][CH:17]=1)=[O:20])[CH2:23]2

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 59331187HCID 59331187, compound

Product 1

HCID 59331184HCID 59331184, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

4-(trifluoromethyl)phenylboronic acid (20.9 mg, 0.11 mmol) was added to a flask charged with (S)-4-iodo-N-(quinuclidin-3-yl)benzamide (35.6 mg, 0.1 mmol), cesium carbonate (81.5 mg, 0.25 mmol) in 2 ml of Acetonitrile and 2 ml of water. The mixture was degassed by sonication for 20 minutes followed by charging catalytic amount of Palladium (II) acetate and place under nitrogen to stirred for 3 hours. The reaction mixture was filtered through pad of celite and washed with acetone, solution was concentrated under vacuum to oil. Preparative HPLC instrument was used to obtain pure (S)—N-(quinuclidin-3-yl)-4′-(trifluoromethyl)biphenyl-4-carboxamide (24.5 mg, 65% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.80 (d, J=8 Hz, 2H), 7.63 (m, 4H), 7.58 (d, J=8 Hz, 2H), 6.33 (d, 1H), 4.11 (m, 1H), 3.38 (m, 1H), 2.80 (m, 4H), 2.56 (ddd, J=6, 14, 6 Hz, 1H), 2.00 (m, 1H), 1.65 (m, 3H), 1.47 (m, 1H). C21H21F3N2O=374.16 LCMS (M+H): m/z 375

Workup

  1. customThe mixture was degassed by sonication for 20 minutes
  2. filtrationThe reaction mixture was filtered through pad of celite
  3. washwashed with acetone, solution
  4. concentrationwas concentrated under vacuum to oil

Sources & evidence

ORD record
ord-a6de2663f7564fb08ae13bd49c9256d7
Source dataset
uspto-grants-2013_05
Patent number
US08435762B2

Reaction notes

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