Cesium carbonate → HCID 58958594, compound

HRID 915602Notes

Reaction equation

HRID 915602 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1Br)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([C:30]1[CH:34]=[C:33]([NH2:35])[N:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH3:42])[N:31]=1)([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:35][C:33]1[N:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH3:42])[N:31]=[C:30]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:34]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 7706433-tert-Butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine2×HCID 3731394N,N-dibenzyl-2-bromobenzenesulfonamide

Product 1

HCID 58958594HCID 58958594, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

N,N-Dibenzyl-2-bromobenzenesulfonamide (from Step 1, 333 mg, 0.80 mmol), 3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (Intermediate C), cesium carbonate (365 mg, 1.12 mmol), Pd2dba3 (41.4 mg, 0.04 mmol), and BINAP (49.8 mg, 0.08 mmol) were dissolved in toluene (7 mL) under nitrogen, and the flask was heated at 110° C. for 20 h. The reaction mixture was cooled to rt, and the solid residue removed by filtration. The solvent was removed under reduced pressure and the residue purified via silica gel flash chromatography using EtOAc/hexane (1:12, v/v) to afford the title compound as a viscous oil (348 mg, 77%). 1H NMR (400 MHz, CDCl3) δ 1.40 (s, 9H), 2.03 (s, 3H), 3.99 (s, 4H), 6.10 (s, 1H), 6.88 (m, 4H), 7.07 (m, 1H), 7.10-7.27 (m, 10H), 7.38 (d, 1H), 7.47 (t, 1H), 7.71 (s, 1H), 7.77 (d, 1H). ES-MS m/z 565.4 (MH)+; HPLC RT (min) 4.37.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe solid residue removed by filtration
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified via silica gel flash chromatography

Sources & evidence

ORD record
ord-da19d40e49494f96896c0c92dc16087a
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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