Boron tribromide → HCID 87191995, compound

HRID 2089031Notes

Reaction equation

HRID 2089031 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([O:24]C)[CH:22]=3)[N:17]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:16]=2)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([OH:24])[CH:22]=3)[N:17]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:27])=[O:28])[CH:16]=2)[CH:5]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 87192444HCID 87192444, compound

Product 1

HCID 87191995HCID 87191995, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 178a (250.0 mg, 0.503 mmol) in CH2Cl2 (20 mL) was added 1M BBr3 in dichloromethane (3.0 mL, 3.02 mmol) at −78° C. The reaction was slowly warmed to room temperature overnight. The clear solution was decanted. The solids remaining in the flask were stirred in saturated NaHCO3 and EtOAc till all the solids were dissolved. The organic layer was dried over MgSO4, filtered, concentrated, and purified on an 80 g column using the ISCO Companion flash system eluting with CH2Cl2/EtOAc (90:10 to 85:15) to give 0.166 g of the title compound.

Workup

  1. customThe clear solution was decanted
  2. dissolutionEtOAc till all the solids were dissolved
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on an 80 g column
  7. washeluting with CH2Cl2/EtOAc (90:10 to 85:15)

Sources & evidence

ORD record
ord-2a089b5f5f4a49529d4de099ced8517a
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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