Boron tribromide → 9-(8-Aza-bicyclo[3.2.1]oct-3-yl)-6-pyridin-3-yl-9H-xanthen-4-ol

HRID 733417Notes

Reaction equation

HRID 733417 reaction equation
C[O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[O:5][C:6]1[CH:7]=[C:8]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH:9]=[CH:10][C:11]=1[CH:12]2[CH:17]1[CH2:23][CH:22]2[NH:24][CH:19]([CH2:20][CH2:21]2)[CH2:18]1.B(Br)(Br)Br>C(Cl)Cl>[CH:22]12[NH:24][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH:17]([CH:12]1[C:13]3[CH:14]=[CH:15][CH:16]=[C:3]([OH:2])[C:4]=3[O:5][C:6]3[C:11]1=[CH:10][CH:9]=[C:8]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[CH:7]=3)[CH2:23]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 116898213-(5-Methoxy-3-pyridin-3-yl-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]octane2×

Product 1

HCID 117179389-(8-Aza-bicyclo[3.2.1]oct-3-yl)-6-pyridin-3-yl-9H-xanthen-4-olYield 4.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(5-methoxy-3-pyridin-3-yl-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]octane, 7k (0.3 g, 0.803 mmol) in CH2Cl2 (20 mL) was added dropwise a 1M BBr3 solution in methylene chloride (3.2 mL, 3.2 mmol) at 0° C. The mixture was stirred at rt for 24 h, and quenched with a saturated NaHCO3 solution (20 mL). The organic layer was dried over MgSO4 and concentrated. The crude product was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA) to yield 20 mg (4.1%) of title compound 9-(8-aza-bicyclo[3.2.1]oct-3-yl)-6-pyridin-3-yl-9H-xanthen-4-ol, 8k as a TFA salt. MS m/z (MH+) 385.2.

Workup

  1. customquenched with a saturated NaHCO3 solution (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified via reverse phase HPLC (eluent: CH3CN in water containing 0.1% TFA)

Sources & evidence

ORD record
ord-5af3e2bc4f6e4222ad41a24ce704d05c
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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