Dichloromethane → HCID 68814838, compound

HRID 730587Notes

Reaction equation

HRID 730587 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13](Br)=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].B[C:27]1[CH:31]=[CH:30][N:29]([Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])[CH:28]=1.ClCCl.C(=O)([O-])[O-].[Cs+].[Cs+]>C(COC)OC.O>[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13]([C:27]3[CH:31]=[CH:30][N:29]([Si:32]([CH:36]([CH3:38])[CH3:37])([CH:39]([CH3:41])[CH3:40])[CH:33]([CH3:34])[CH3:35])[CH:28]=3)=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 57834992HCID 57834992, compoundHCID 178419152HCID 178419152, compound

Product 1

HCID 68814838HCID 68814838, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To 10 mL of a 9:1 mixture of dimethoxyethane/water was added 3-benzyl-7-bromo-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester (0.719 g, 1.783 mmol), 3-boranyl-1-triisopropylsilanyl-1H-pyrrole (0.476 g, 1.783 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (69.7 mg, 0.089 mmol), and cesium carbonate (0.697 g, 2.139 mmol.) The resulting suspension was vacuum-purged with argon and heated to 85° C. for 1 hour. The reaction mixture was added to 100 mL of 1:1 water/ethyl acetate and the organic layer was separated. The combined organic fractions were washed with 100 mL each of water and brine and dried over sodium sulfate. Concentration in vacuo gave a crude solid which was purified by flash chromatography (0 to 10% gradient ethyl acetate in hexanes) to give 0.750 g of 3-benzyl-2-oxo-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester as a white solid. MS: 446 (M−BOC+H)+.

Workup

  1. customwas vacuum-purged with argon
  2. additionThe reaction mixture was added to 100 mL of 1:1 water/ethyl acetate
  3. customthe organic layer was separated
  4. washThe combined organic fractions were washed with 100 mL each of water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration in vacuo
  7. customgave a crude solid which
  8. customwas purified by flash chromatography (0 to 10% gradient ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-21b7d6295fb5455f8ee31e610a302265
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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