Ethyl Acetate → HCID 68313323, compound

HRID 1914875Notes

Reaction equation

HRID 1914875 reaction equation
[NH2:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:5]2[N:6]([C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=3[F:17])[C:7](=[O:9])[NH:8][C:4]=2[C:3]=1[O:22]C.C(OCC)(=O)C>C(Cl)Cl.CCCCCC>[NH2:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:5]2[N:6]([C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=3[F:17])[C:7](=[O:9])[NH:8][C:4]=2[C:3]=1[OH:22]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 68313298HCID 68313298, compound

Product 1

HCID 68313323HCID 68313323, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

1.0M Solution of borontribromide in DCM (6.4 mL, 6.4 mmol) was added to a solution of 5-amino-6,7-difluoro-1-(2-fluoro-4-iodo-phenyl)-4-methoxy-1,3-dihydro-benzoimidazol-2-one (I-11a: 1.4 g, 3.2 mmol) in DCM (50 mL) at 0° C. and the resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (80% ethyl acetate in hexane). The reaction mixture was quenched with water and stirred for 1 hour. The aqueous layer was extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated to afford 1.15 g of the product (85.1% yield).

Workup

  1. customThe reaction mixture was quenched with water
  2. stirringstirred for 1 hour
  3. extractionThe aqueous layer was extracted with ethyl acetate (100 mL×2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0bf12827e97e4546928c16369bf1df67
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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