Dimethylformamide → HCID 67155953, compound

HRID 2196702Notes

Reaction equation

HRID 2196702 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4](S(C2C=CC=CC=2)(=O)=O)[CH:3]=1.CN.[CH3:25][N:26](C=O)[CH3:27]>O>[CH3:25][N:26]([CH3:27])[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6329MethylamineHCID 67155858HCID 67155858, compound

Product 1

HCID 67155953HCID 67155953, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

3-Bromo-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (200 mg, 0.523 mmol) and methylamine (1.31 mL, 10.47 mmol, 40% solution in water) were combined with DMF (1 mL) in a microwave vessel and heated to 150° C. in a microwave reactor for one hour. The mixture was then diluted with water, extracted with EtOAc, extracts dried over sodium sulfate and concentrated under reduced pressure. Sep Pak purification (10 g cartridge, 1:1 ethyl acetate:hexanes to 100% ethyl acetate) afforded N,N-dimethyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-3-amine as a solid (55 mg, 51%). 1H NMR (400 MHz, d6-DMSO) δ 12.03 (br s, 1H), 8.70-8.72 (m, 1H), 8.20-8.23 (m, 1H), 5.46-5.47 (m, 1H), 2.98 (s, 6H); (APCI-pos) M+1=207.2.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialextracts dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customSep Pak purification (10 g cartridge, 1:1 ethyl acetate:hexanes to 100% ethyl acetate)

Sources & evidence

ORD record
ord-167c6f3200d047e59421ca3f519c7450
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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