Boron tribromide → HCID 178490843, compound

HRID 1050422Notes

Reaction equation

HRID 1050422 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[C:9](=[O:26])[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:11]3([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:4]=12.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[C:9](=[O:26])[N:10]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[C:11]3([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:4]=12

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118598676HCID 118598676, compound

Product 1

HCID 178490843HCID 178490843, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of 4′-methoxy-6′-(4-methoxybenzyl)spiro[cyclohexane-1,5′-pyrrolo[3,4-b]pyridin]-7′(6′H)-one (4, 1.0 mmol, 1 eq) in dichloromethane (25 mL) with boron tribromide (2.0 mmol, 2 eq) at 0° C. Stir the mixture for 2 h at room temperature and quench with water at 0° C. Extract the mixture with ethyl acetate and remove the solvent under reduced pressure to get the crude. Purity the crude by silica gel column chromatography to get 4′-hydroxy-6′-(4-methoxybenzyl)spiro[cyclohexane-1,5′-pyrrolo[3,4-b]pyridin]-7′(6′H)-one (5).

Workup

  1. customquench with water at 0° C
  2. extractionExtract the mixture with ethyl acetate
  3. customremove the solvent under reduced pressure
  4. customto get the crude

Sources & evidence

ORD record
ord-e2a83c73e0384d2c8e3157fc6ac5eae1
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

Loading…