Water → (S)-4-(5,7-dibromo-2,3-dihydro-1H-indol-1-yl)-1-[1-(methoxymethyl)-3-methoxypropyl]-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine

HRID 1066751Notes

Reaction equation

Cl[C:2]1[C:7]2[N:8]=[N:9][N:10]([C@H:11]([CH2:16][O:17][CH3:18])[CH2:12][CH2:13][O:14][CH3:15])[C:6]=2[CH:5]=[C:4]([CH3:19])[N:3]=1.[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([Br:30])[CH:29]=1)[NH:26][CH2:25][CH2:24]2.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O>C1COCC1>[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([Br:30])[CH:29]=1)[N:26]([C:2]1[C:7]3[N:8]=[N:9][N:10]([C@H:11]([CH2:16][O:17][CH3:18])[CH2:12][CH2:13][O:14][CH3:15])[C:6]=3[CH:5]=[C:4]([CH3:19])[N:3]=1)[CH2:25][CH2:24]2

Participants

Conditions

Temperature: 25 °C

Procedure

(S)-4-chloro-1-(1-methoxymethyl-3-methoxypropyl)-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine (0.72 g, 2.54 mmol) and 5,7-dibromoindoline (0.72 g, 2.60 mmol) were dissolved in anhydrous THF (6 mL) and cooled in an ice bath. To that a 1 M solution of NaHMDS in THF (3.0 mL, 3.0 mmol) was added and the reaction was stirred for 20 min, allowed to warm to 25° C. and stirred for 3 h. Then water (30 mL) was added and the mixture was extracted twice with EtOAc (80 and 40 mL). The combined organic extracts was washed with brine (30 mL) dried (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 40% EtOAc/hexanes as eluent to give the product (1.14 g, 85% yield).

Workup

temperaturecooled in an ice bath
stirringstirred for 3 h
extractionthe mixture was extracted twice with EtOAc (80 and 40 mL)
washThe combined organic extracts was washed with brine (30 mL)
dry with materialdried (MgSO4)
customThe residue was chromatographed on silica gel using 40% EtOAc/hexanes as eluent

Sources & evidence

ORD record: ord-d07436b75e014f1da87edb4857051949
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245769B1

Reaction notes

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