1-Biphenyl-2-ylmethyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine → 1-Biphenyl-2-ylmethyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-ol

HRID 1445931Notes

Reaction equation

[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([O:17]C)[C:11]=2[CH:10]=[C:9]1[CH3:19]>CC(O)=O.Br>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[CH:15]=[CH:14][NH:13][C:12](=[O:17])[C:11]=2[CH:10]=[C:9]1[CH3:19]

Participants

Conditions

Temperature: 105 °C

Procedure

To a stirred solution of 1-biphenyl-2-ylmethyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine 4 (370 mg, 1.13 mmol) in AcOH (15 mL), 48% of HBr (5 mL) was added. The reaction mixture was heated to 105° C., and then stirred for 16 h, cooled to room temperature and evaporated. The obtained residue was dissolved in CH2Cl2 (100 mL), washed with saturated NaHCO3 (30 mL), brine (30 mL), dried over Na2SO4 and evaporated to afford crude product 5, which was used without further purification for next step. Yield: 355 mg (100%).

Workup

temperaturecooled to room temperature
customevaporated
dissolutionThe obtained residue was dissolved in CH2Cl2 (100 mL)
washwashed with saturated NaHCO3 (30 mL), brine (30 mL)
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-080d03cc8c944c87a9432e73dc6a5c27
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666898B2

Reaction notes

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