Dimethylformamide → N-(3-(5-Nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)phenyl)acetamide

HRID 502800Notes

Reaction equation

HRID 502800 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].[NH2:7][C:8]1[C:13]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19](NC(=O)C)=[CH:18][CH:17]=2)=[CH:12][C:11]([N+:26]([O-:28])=[O:27])=[CH:10][N:9]=1.O1CCCC1.C[N:35](C)C=O>>[N+:26]([C:11]1[CH:12]=[C:13]2[CH:14]=[C:15]([C:16]3[CH:17]=[C:18]([NH:35][C:2](=[O:4])[CH3:1])[CH:19]=[CH:20][CH:21]=3)[NH:7][C:8]2=[N:9][CH:10]=1)([O-:28])=[O:27]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 68462435N-[4-(2-amino-5-nitro-pyridin-3-ylethynyl)-phenyl]-acetamide

Product 1

HCID 68462732N-(3-(5-Nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)phenyl)acetamideYield 68%

Conditions

Temperature
70 °C

Procedure

Potassium tert-butoxide (2.25 g, 20 mmol) was added to a solution of N-[4-(2-amino-5-nitro-pyridin-3-ylethynyl)-phenyl]-acetamide (1.48 g, 5 mmol) in a 2:1 mixture of tetrahydrofuran and dimethylformamide (75 mL). The mixture was heated at 70° C. for 16 hours then the tetrahydrofuran was removed in vacuo. The mixture was poured onto a pad of silica and eluted with 10% methanol in ethyl acetate. The organics were concentrated in vacuo to 5% of their original volume and water (30 mL) was added. The resultant orange solid was filtered and dried to afford N-[3-(5-Nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)-phenyl]-acetamide (1.01 g, 68%).

Workup

  1. customthe tetrahydrofuran was removed in vacuo
  2. additionThe mixture was poured onto a pad of silica
  3. washeluted with 10% methanol in ethyl acetate
  4. concentrationThe organics were concentrated in vacuo to 5% of their original volume and water (30 mL)
  5. additionwas added
  6. filtrationThe resultant orange solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-2e4c0ac1435a484f98c22a459d2edea3
Source dataset
uspto-grants-2010_08
Patent number
US07776878B2

Reaction notes

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