Boron tribromide → HCID 59700152, compound

HRID 901520Notes

Reaction equation

HRID 901520 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)[CH:18]=2)[NH:13][CH:12]=1.B(Br)(Br)Br>ClCCl>[OH:26][C:22]1[CH:21]=[C:20]([C:17]2[CH:18]=[C:19]3[C:11]([C:4]4[C:5]([OH:9])=[CH:6][CH:7]=[CH:8][C:3]=4[OH:2])=[CH:12][NH:13][C:14]3=[N:15][CH:16]=2)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59699929HCID 59699929, compound

Product 1

HCID 59700152HCID 59700152, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-[3-(2,6-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]-phenol (23 mg, 0.066 mmol) in dichloromethane (1 mL) at −78° C. was added 1 M boron tribromide solution in dichloromethane (0.23 mL, 0.23 mmol) dropwise. The reaction mixture was warmed up to room temperature over 4 h, then quenched with water and neutralized to pH8 with a saturated solution of aqueous sodium bicarbonate. The mixture was extracted with EtOAc three times and the extracts were combined and adsorbed on silica gel. Purification on silica gel with a gradient of methanol/dichloromethane afforded 2-[5-(3-hydroxy-phenyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]-benzene-1,3-diol as a beige solid (17 mg, 81% yield). 1H NMR (500 MHz, DMSO-d6) δ 6.43 (d, J=8.0 Hz, 1H), 6.73 (dd, J=2.5, 7.5 Hz, 1H), 6.91 (t, J=8.0 Hz, 1H), 7.00 (t, J=2.0 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 7.24 (t, J=8.0 Hz, 1H), 7.46 (d, J=2.5 Hz, 1H), 7.85 (d, J=2.0 Hz, 1H), 8.42 (d, J=2.0 Hz, 1H), 9.10 (broad s, 2H), 9.49 (broad s, 1H), 11.7 (s, 1H). MS: m/z 319 (M+H+).

Workup

  1. customquenched with water and neutralized to pH8 with a saturated solution of aqueous sodium bicarbonate
  2. extractionThe mixture was extracted with EtOAc three times
  3. customPurification on silica gel with a gradient of methanol/dichloromethane

Sources & evidence

ORD record
ord-552dfe60a2df496aa7657919af24e019
Source dataset
uspto-grants-2008_04
Patent number
US07361764B2

Reaction notes

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