Potassium Hydroxide → 3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide

HRID 2234686Notes

Reaction equation

HRID 2234686 reaction equation
[F:1][C:2]1[C:3]([NH:40][CH2:41][C:42]2[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=2)=[C:4]([CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[CH:20][N:19](S(C4C=CC(C)=CC=4)(=O)=O)[C:16]3=[N:17][CH:18]=2)[CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].[OH-].[K+]>O1CCCC1.CO>[F:1][C:2]1[C:3]([NH:40][CH2:41][C:42]2[CH:43]=[CH:44][N:45]=[CH:46][CH:47]=2)=[C:4]([CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 577315803-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide

Product 1

HCID 577314363-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide was dissolved in a mixture of tetrahydrofuran and methanol. A solution of aqueous potassium hydroxide (50% w/v) was added to the reaction mixture, and the combined mixture was allowed to stir for 1 hour at room temperature. The reaction mixture was quenched with sodium bicarbonate solution, and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (0-100% [10% methanol in ethyl acetate] in hexanes) to afford 3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide. 1H-NMR (250 MHz, DMSO-d6) δ 11.87 (s, 1H), 8.53-8.41 (m, 3H), 8.09 (d, J=2.0 Hz, 1H), 7.70 (d, J=2.6 Hz, 1H), 7.60 (dd, J=7.5, 1.5 Hz, 1H), 7.52 (dd, J=14.0, 2.0 Hz, 1H), 7.33-7.21 (m, 3H), 7.17 (d, J=1.6 Hz, 1H), 7.11 (d, J=7.9 Hz, 1H), 7.04 (t, J=7.4 Hz, 1H), 6.01 (broad s, 1H), 4.42 (d, J=6.6 Hz, 2H), 3.80 (s, 3H), 2.89 (s, 12H), 2.59 (s, 12H); MS: m/z 496.3 (M+H+).

Workup

  1. customThe reaction mixture was quenched with sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (0-100% [10% methanol in ethyl acetate] in hexanes)

Sources & evidence

ORD record
ord-7abbb4d9a36e4a71b4e98c175e2c8d60
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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