Boron tribromide → HCID 66915484, compound

HRID 656481Notes

Reaction equation

HRID 656481 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]32[CH2:17][CH2:16][CH2:15][N:14]2[CH:18]=[N:19][CH:20]=[C:13]32)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[C:10]12([CH2:17][CH2:16][CH2:15][N:14]3[CH:18]=[N:19][CH:20]=[C:13]13)[C:11]1[C:6](=[CH:5][CH:4]=[C:3]([OH:2])[CH:12]=1)[CH2:7][CH2:8][CH2:9]2

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 15979313HCID 15979313, compound

Product 1

HCID 66915484HCID 66915484, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

7.450 mmol of 7′-methoxy-3′,4′,6,7-tetrahydro-2′H,5H-spiro[imidazo[1,5-a]pyridine-8,1′-naphthalene] (Example 1) are introduced at 0° C. into 50 ml of dichloromethane. 18.630 mmol of boron tribromide (1M in dichloromethane) are added dropwise over 20 minutes. The reaction mixture is subsequently stirred at 0° C. for 3 hours. It is admixed with 50 ml of saturated aqueous sodium bicarbonate solution and stirred thoroughly for 30 minutes. The organic phase is separated off and the aqueous phase is extracted with 30 ml of dichloromethane. The combined organic phases are dried with magnesium sulphate and evaporated. The title compound is obtained as a yellow foam. The crude title compound is reacted further without further purification. Rf=0.28 (dichlormethane-ethanol=95:5); Rt=5.22.

Workup

  1. stirringstirred thoroughly for 30 minutes
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted with 30 ml of dichloromethane
  4. dry with materialThe combined organic phases are dried with magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-460ac2950cc74c63beb519a2b8858759
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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