Sodium Carbonate → HCID 68705441, compound

HRID 1988858Notes

Reaction equation

Cl.[CH2:2]([N:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([Br:27])[C:16]=2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:11]([CH3:28])=[C:10]1[CH3:29])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:2]([N:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([Br:27])[C:16]=2[O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[C:11]([CH3:28])=[C:10]1[CH3:29])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 10340Sodium Carbonate

HCID 68705958HCID 68705958, compound

Product 1

HCID 68705441HCID 68705441, compound

Procedure

1-Benzyl-6-bromo-7-(4-fluorobenzyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine hydrochloride prepared in Example 273 was neutralized with a saturated sodium carbonate solution to obtain 1-benzyl-6-bromo-7-(4-fluoro-benzyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (1.4 g, 3.18 mmol). A solution of 1-benzyl-6-bromo-7-(4-fluoro-benzyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (1.4 g, 3.18 mmol) and copper (I) cyanide (700 mg, 7.52 mmol) in anhydrous N,N-dimethylformamide (30 ml) was refluxed for 48 hours and then cooled to room temperature. Ethyl acetate was added to the reaction mixture, which was then filtered to discard insoluble solid. Water was added to the resulting solution, which was then extracted with ethyl acetate. The resulting organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/methanol=10/1, v/v) to give 278 mg of the titled compound as a white solid.

Sources & evidence

ORD record: ord-e970035d45df4873a533fb0f7be90f47
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642269B2

Reaction notes

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