Methyl iodide → HCID 59811527, compound

HRID 2113784Notes

Reaction equation

Br[C:2]1[N:3]([CH3:19])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][N:6]2[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18].[CH2:20]([Li])CCC.IC>C1COCC1.CCCCCC>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[N:6]1[CH2:7][CH2:8][CH2:9][C:10]2=[C:2]([CH3:20])[N:3]([CH3:19])[N:4]=[C:5]12

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3-bromo-7-(2,4-dichloro-phenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine (1-2; 0.100 g, 0.277 mmol) in 2 mL of dry THF was cooled to −78° C. in a dry ice-acetone bath under an argon atmosphere and treated with 0.21 mL of 1.6 M n-butyllithium in hexane. After 10 m the mixture was treated with iodomethane (0.21 mL, 0.047 g, 0.33 mmol) and stirred at −78° C. for 1 h and allowed to come to room temperature overnight. The reaction mixture was quenched with 40 mL of saturated ammonium chloride and extracted twice with 25 mL portions of ethyl acetate. The combined the extracts were washed with brine, dried over magnesium sulfate, and evaporated to dryness to yield 79 mg of crude product. Purification by preparative TLC using ethyl acetate/toluene (1:9) afforded 19 mg of 7-(2,4-dichloro-phenyl)-2,3-dimethyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine (2-17; 23% theory) as a pink solid: mp 66.6-76.6° C.

Workup

waitto come to room temperature overnight
customThe reaction mixture was quenched with 40 mL of saturated ammonium chloride
extractionextracted twice with 25 mL portions of ethyl acetate
washwere washed with brine
dry with materialdried over magnesium sulfate
customevaporated to dryness
customto yield 79 mg of crude product
customPurification by preparative TLC

Sources & evidence

ORD record: ord-f1f2806fe5da4258be004736ca82b40e
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432283B2

Reaction notes

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