Sodium Iodide → 3-(1-(4-(2-methoxyethoxy)-2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-bromopyridin-2-amine

HRID 446739Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[C:14]=3[F:21])[N:11]=[N:10][N:9]=2)=[CH:6][C:5]([Br:22])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:29][O:30][CH2:31][CH2:32]Br.[I-].[Na+]>[Cl-].[Na+].O.O.CCOC(C)=O>[CH3:29][O:30][CH2:31][CH2:32][O:19][C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:8]([C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([Br:22])[CH:6]=3)=[N:9][N:10]=[N:11]2)=[C:14]([F:21])[C:15]=1[F:20]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred suspension of Compound 1086 (300 mg, 0.8127 mmol), potassium carbonate (224.6 mg, 1.625 mmol), and 2-bromoethyl methyl ether (169.4 mg, 114.5 μL, 1.219 mmol) was added sodium iodide (182.7 mg, 1.219 mmol). The reaction mixture was heated to 50° C. and allowed to stir overnight. After cooling, the mixture was partioned between EtOAc and water. The organics were with brine, dried over sodium sulfate, and the volatiles removed in vacuo. Purification by silica gel chromatography (0-50% gradient of EtOAc/hexanes) gave 3-(1-(4-(2-methoxyethoxy)-2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-bromopyridin-2-amine (Compound 1089, 120 mg).

Workup

temperatureAfter cooling
dry with materialdried over sodium sulfate
customthe volatiles removed in vacuo
customPurification by silica gel chromatography (0-50% gradient of EtOAc/hexanes)

Sources & evidence

ORD record: ord-fd172515c29e41fb8dfa831b70645d41
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481524B2

Reaction notes

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