Boron tribromide → HCID 22339542, compound

HRID 585131Notes

Reaction equation

HRID 585131 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([N:32]2[C:37](=[O:38])[N:36](COCC[Si](C)(C)C)[C:35](=[O:47])[CH:34]=[N:33]2)[CH:29]=[C:28]([Cl:48])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:26]C)=[C:9]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)=[O:13])[CH:10]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:31]=[C:30]([N:32]2[C:37](=[O:38])[NH:36][C:35](=[O:47])[CH:34]=[N:33]2)[CH:29]=[C:28]([Cl:48])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:26])=[C:9]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:17][CH:16]=2)=[O:13])[CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22339669HCID 22339669, compound

Product 1

HCID 22339542HCID 22339542, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{5-[2,6-dichloro-4-(3,5-dioxo-4-(2-trimethylsilanyl-ethoxy-methyl)4,5-dihydro-3H-[1,2,4]triazin-2-yl)-phenoxy]-2-methoxy-phenyl}-3-(4-trifluoromethoxy-phenyl)-urea (72 mg, 0.1 mmol) in CH2Cl2 was added dropwise BBr3 (1M in CH2Cl2, 4.0 mL, 0.4 mmol). The mixture was stirred at room temperature for 18 h and quenched with water (10 mL). After stirring at room temperature for 1 h, the quenched mixture was extracted with CH2Cl2 (3×10 mL). The combined CH2Cl2 extracts were dried and concentrated. The residue was purified by preparative TLC (10% MeOH in CH2Cl2) to afford the title compound (25.4 mg) of this EXAMPLE. MS Calc.:584.3 Found:581.8 (M−1).

Workup

  1. customquenched with water (10 mL)
  2. stirringAfter stirring at room temperature for 1 h
  3. extractionthe quenched mixture was extracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined CH2Cl2 extracts were dried
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-036e71ffea594e21b7a21cab1d16f049
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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