Cesium carbonate → HCID 68816272, compound

HRID 735020Notes

Reaction equation

HRID 735020 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].I[C:8]1[CH:13]=[CH:12][C:11]([C:14]2([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:42])[C:40]#[CH:41])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1>C1COCC1.[Cu]I>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:42])[C:40]#[C:41][C:8]3[CH:13]=[CH:12][C:11]([C:14]4([NH:17][C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])[CH2:16][CH2:15]4)=[CH:10][CH:9]=3)=[CH:34][CH:33]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 59019959tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamateHCID 86060771Propynoic acid-(4'-chlorobiphenyl-4-yl)amide

Product 1

HCID 68816272HCID 68816272, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.4 g (4.2 mmol) of cesium carbonate and 0.5 g (1.4 mmol) of tert-butyl [1-(4-iodophenyl)cyclopropyl]carbamate are placed in 20 mL of THF and cooled to −15° C. in the ice/methanol bath, rinsed with argon, and degassed. To this reaction mixture is added successively 160 mg (0.14 mmol) of tetrakistriphenylphosphine palladium and 30 mg (0.158 mmol) of copper (I) iodide and the mixture is again degassed. 0.5 g (1.4 mmol) of propynoic acid-(4′-chlorobiphenyl-4-yl)amide is finally added. The mixture is stirred for 24 hours at ambient temperature and the reaction mixture is then evaporated down. The residue is triturated with water and ethyl acetate, suction filtered, washed with ethyl acetate, and dried in the air. Yield: 0.4 g (59% of theory); C29H27ClN2O3 (M=486.99); calc.: molecular ion peak (M+H)+: 487/89 (Cl); found: molecular ion peak (M+H)+: 487/89 (Cl); Rf value: 0.62 (silica gel, cyclohexane/ethyl acetate (1:1)).

Workup

  1. washrinsed with argon
  2. customdegassed
  3. customthe mixture is again degassed
  4. customthe reaction mixture is then evaporated down
  5. customThe residue is triturated with water and ethyl acetate, suction
  6. filtrationfiltered
  7. washwashed with ethyl acetate
  8. customdried in the air

Sources & evidence

ORD record
ord-7827551ac0e84c6aa6b7c7dbc7a85bef
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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