Nitrogen → HCID 71003969, compound

HRID 2201753Notes

Reaction equation

HRID 2201753 reaction equation
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17]C)[CH:15]=2)[C:10](=[O:19])[N:9]1C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.N#N>ClCCl>[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10](=[O:19])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 25134Boron tribromideHCID 86692160HCID 86692160, compound

Product 1

HCID 71003969HCID 71003969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cold (−5° C.-1-10° C.) solution of tert-butyl 3-benzyl-5-methoxy-1-oxoisoindoline-2-carboxylate (0.92 g, 2.59 mmol) in dichloromethane (9 mL) was added BBr3 (7.8 mL, 7.78 mmol) dropwise under N2. This was stirred at −5° C. for 3 hours, then room temperature for overnight. TLC showed complete conversion. The reaction mixture was poured into ice-water, extracted 3× with dichloromethane. The combined organic layer was washed 1× with water, 1× with saturated NaHCO3, 1× with saturated NaCl solution, dried over Na2SO4, concentrated down to a light yellow solid (620 mg, 100%).

Workup

  1. stirringThis was stirred at −5° C. for 3 hours
  2. extractionextracted 3× with dichloromethane
  3. washThe combined organic layer was washed 1× with water, 1× with saturated NaHCO3, 1× with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated down to a light yellow solid (620 mg, 100%)

Sources & evidence

ORD record
ord-002446527f0141ec80789f9503efd417
Source dataset
uspto-grants-2016_06
Patent number
US09365512B2

Reaction notes

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