Cesium carbonate → HCID 86719136, compound

HRID 1844722Notes

Reaction equation

HRID 1844722 reaction equation
Br[C:2]1[N:6]([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[C:5]([CH3:14])=[C:4]([S:15]([NH:18][CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])(=[O:17])=[O:16])[CH:3]=1.[C:27]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][C:36]=1[C:50]([CH3:53])([CH3:52])[CH3:51])(=[O:34])=[O:33])([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:50]([C:36]1[CH:37]=[C:38]([C:2]2[N:6]([CH2:7][CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[C:5]([CH3:14])=[C:4]([S:15]([NH:18][CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])(=[O:17])=[O:16])[CH:3]=2)[CH:39]=[CH:40][C:35]=1[S:32](=[O:33])(=[O:34])[NH:31][C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:53])([CH3:51])[CH3:52]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 70869316HCID 70869316, compoundHCID 70874984HCID 70874984, compound

Product 1

HCID 86719136HCID 86719136, compoundYield 44.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of bromide 10a (100 mg, 0.22 mmol), boronic ester P19 (106 mg, 0.27 mmol), Cs2CO3 (181 mg, 0.56 mmol) and Pd(dppf)Cl2 (50 mg) in dioxane and water (10:1, 100 mL) was heated at 100° C. overnight. The solvent was removed, diluted with water, extracted with EA (3×), the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give product 10 (62 mg, 44%) as yellow solid.

Workup

  1. customThe solvent was removed
  2. additiondiluted with water
  3. extractionextracted with EA (3×)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9a486e11b70f46f184ef4c4e1616f868
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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