Boron tribromide → HCID 59843047, compound

HRID 1878780Notes

Reaction equation

HRID 1878780 reaction equation
C[O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:9]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 49657626HCID 49657626, compound

Product 1

HCID 59843047HCID 59843047, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 2-(4-methoxybenzyl)-6-phenylpyridazin-3(2H)-one (400 mg, 1368 mmol) in DCM (2.5 mL) at 0° C. under nitrogen was added boron tribromide (1294 μl, 13683 μmol) drop-wise over a 1 minute period. More DCM (10 mL) was added to the reaction to create a suspension and ice bath removed. After 3 hours, the reaction was chilled to 0° C. and quenched with methanol (5 mL). The pH was then adjusted to 14 with NaOH (1 M), then adjusted to 7 with HCl (5 M). The aqueous layer was then extracted 3× with 9:1 CHCl3/IPA (50 mL). The combined organics were then dried with sat NH4Cl and MgSO4. The organic was then concentrated onto dry silica (20 g) and purified on silica (40 g) eluting with 20>40% of EtOAc/DCM. Product was isolated as a white solid. MS (ESI pos. ion) calc'd for C17H14N2O2: 278; found 279 (MH+). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.21 (s, 2 H) 6.68-6.77 (m, 2 H) 7.06 (d, J=9.78 Hz, 1H) 7.22 (d, J=8.61 Hz, 2 H) 7.40-7.55 (m, 3 H) 7.89 (dd, J=8.22, 1.37 Hz, 2 H) 8.04 (d, J=9.78 Hz, 1 H) 9.42 (s, 1 H).

Workup

  1. customremoved
  2. customquenched with methanol (5 mL)
  3. extractionThe aqueous layer was then extracted 3× with 9:1 CHCl3/IPA (50 mL)
  4. dry with materialThe combined organics were then dried with sat NH4Cl and MgSO4
  5. concentrationThe organic was then concentrated onto dry silica (20 g)
  6. custompurified on silica (40 g)
  7. washeluting with 20>40% of EtOAc/DCM
  8. customProduct was isolated as a white solid

Sources & evidence

ORD record
ord-a5880f781c0d4cc4a2fbf182e2ecb05b
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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