Dimethylformamide → HCID 178419502, compound

HRID 733387Notes

Reaction equation

HRID 733387 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[NH:4][N:3]=1.[N:12]12[CH2:19][CH:16]([CH2:17][CH2:18]1)[NH:15][CH2:14][CH2:13]2.C(N(CC)CC)C.CN(C)[CH:29]=[O:30]>C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(Cl)Cl)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[BrH:1].[N:12]12[CH2:19][CH:16]([CH2:17][CH2:18]1)[N:15]([C:29]([C:2]1[C:10]3[C:5](=[N:6][C:7]([CH3:11])=[CH:8][CH:9]=3)[NH:4][N:3]=1)=[O:30])[CH2:14][CH2:13]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 123740771,4-Diazabicyclo[3.2.1]octaneHCID 178422500HCID 178422500, compound

Product 1

HCID 178419502HCID 178419502, compound

Reagents, catalysts & solvents 1

HCID 178479802HCID 178479802, compoundCatalyst

Procedure

By analogy with Example 2, 0.7 g (3.3 mmol) of 3-bromo-6-methyl-1H-pyrazolo[3,4-b]pyridine is reacted with 1.1 g (9.9 mmol) of 1,4-diazabicyclo[3.2.1]octane in the presence of 0.35 g (0.5 mmol) of bis(triphenylphosphino)dichloropalladium and 2.3 ml of triethylamine in 10 ml of dimethylformamide under the conditions described for Example 1, giving 0.21 g of product, which is dissolved in 20 ml of acetone before addition of 0.27 ml of a 5.7 N solution of hydrobromic acid in acetic acid. The dihydrobromide crystals are collected by filtration and dried under vacuum.

Sources & evidence

ORD record
ord-7fc7dea91f8a49fa8f939a2768568241
Source dataset
uspto-grants-2009_09
Patent number
US07589201B2

Reaction notes

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