Dimethylformamide → HCID 178481752, compound

HRID 1628037Notes

Reaction equation

HRID 1628037 reaction equation
[CH3:1][N:2]1[C:6]2=[C:7]3[C:13]([C:14]#[N:15])=[CH:12][N:11](S(C4C=CC(C)=CC=4)(=O)=O)[C:8]3=[N:9][CH:10]=[C:5]2[CH:4]=[N:3]1.C1C(=O)N([Br:33])C(=O)C1.CN(C=O)C>O>[Br:33][C:12]1[NH:11][C:8]2=[N:9][CH:10]=[C:5]3[CH:4]=[N:3][N:2]([CH3:1])[C:6]3=[C:7]2[C:13]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimide2×HCID 58382205HCID 58382205, compound

Product 1

HCID 178481752HCID 178481752, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A 10 mL microwave reaction vial was charged with 1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine-8-carbonitrile (0.011 g, 0.30 mmol, prepared using General Procedure AK from Preparation #1, Step D with NBS, General Procedure AE), NBS (0.012 g, 0.66 mmol) and DMF (2 mL). The suspension was heated in a microwave at about 150° C. for about 30 min (250 psi maximum pressure, 2 min ramp, 300 max watts). Additional NBS (134 mg, 0.754 mmol) was added and mixture was stirred at rt for about 2 h. To the reaction mixture was added water (4 mL) and the solid was collected by filtration and washed with water (5 mL). The solid was dried in a vacuum oven at about 70° C. for about 40 min to give 7-bromo-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine-8-carbonitrile (0.036 g, 43%): LC/MS (Table 2, Method c) Rt=1.25 min; MS m/z: 276 (M+H)+.

Workup

  1. customA 10 mL microwave reaction
  2. filtrationthe solid was collected by filtration
  3. washwashed with water (5 mL)
  4. customThe solid was dried in a vacuum oven at about 70° C. for about 40 min

Sources & evidence

ORD record
ord-4d8a330d37dc4faea07362d00eae3c06
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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