Triethylamine → 7-Bromo-6-methoxy-1(2H)-isoquinolinone

HRID 1095293

Reaction equation

HRID 1095293 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/C(O)=O)=[CH:4][C:3]=1[O:13][CH3:14].CC[N:17]([CH2:20]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([CH:8]=[CH:9][NH:17][C:20]2=[O:29])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 580051274-Bromo-3-methoxycinnamic acid

Product 1

HCID 580051257-Bromo-6-methoxy-1(2H)-isoquinolinoneYield 59.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A portion of the product from Step 1 (12.5 g, 48.6 mmol) was azeotroped with benzene and suspended in benzene (94 mL). Et3N (9.49 mL, 68.1 mmol) and diphenylphosphoryl azide (10.48 mL, 48.6 mmol) were added and the reaction mixture stirred at RT for 1 hour. The mixture was filtered through a pad of silica and eluted with ˜1 L of PhMe, the volatiles evaporated, the residue resuspended in diphenylmethane (94 mL) and the mixture heated to reflux for 3 hours (internal temperature 250° C.). The reaction mixture was allowed to cool to RT, stirred overnight, filtered and the solid washed with hexanes (100 mL) to give tan solid (7.4 g). LRMS ESI+ (M+H)+254.1.

Workup

  1. filtrationThe mixture was filtered through a pad of silica
  2. washeluted with ˜1 L of PhMe
  3. customthe volatiles evaporated
  4. temperaturethe mixture heated
  5. temperatureto reflux for 3 hours (internal temperature 250° C.)
  6. temperatureto cool to RT
  7. stirringstirred overnight
  8. filtrationfiltered
  9. washthe solid washed with hexanes (100 mL)

Sources & evidence

ORD record
ord-74128ac1381148d3b10bfcc136020e48
Source dataset
uspto-grants-2012_03
Patent number
US08138164B2

Linked notes

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