Tetrahydrofuran → 3-{3-(4-nitrophenyl)-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-1-yl}-1-propanol

HRID 28936

Reaction equation

HRID 28936 reaction equation
C12BC(CCC1)CCC2.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]4[N:30]([S:33]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)(=[O:35])=[O:34])[CH:31]=[CH:32][C:25]=34)=[CH:22][N:21]([CH2:42][CH:43]=[CH2:44])[N:20]=2)=[CH:15][CH:14]=1)([O-:12])=[O:11].[O:45]1CCCC1>>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]4[N:30]([S:33]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)(=[O:35])=[O:34])[CH:31]=[CH:32][C:25]=34)=[CH:22][N:21]([CH2:42][CH2:43][CH2:44][OH:45])[N:20]=2)=[CH:17][CH:18]=1)([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 689971604-[3-(4-nitrophenyl)-1-(2-propen-1-yl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 689984293-{3-(4-nitrophenyl)-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-1-yl}-1-propanolYield 84%

Procedure

To a solution of 0.5M 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (6.16 mL) cooled to 0° C. was added a solution of 4-[3-(4-nitrophenyl)-1-(2-propen-1-yl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (2.06 mmol) in tetrahydrofuran (14 mL). The reaction mixture was stirred at room temperature under an inert atmosphere for 4.5 h and then re-cooled to 0° C. followed by quenching with water (1.7 mL). After 15 minutes of stirring at 0° C., 6N aqueous sodium hydroxide (1.24 mL) was added dropwise followed by 30% aqueous hydrogen peroxide (0.865 mL). The reaction mixture was stirred for 1.5 h at 0° C., neutralized with 6N aqueous hydrochloric acid and concentrated in vacuo. Water (10 mL) was added to the residue and the solution extracted with ethyl acetate (3×15 mL), the combined organic layers dried over magnesium sulfate and concentrated in vacuo to afford the title compound (84%). ESMS [M+H]+: 504.2

Workup

  1. temperaturere-cooled to 0° C.
  2. customby quenching with water (1.7 mL)
  3. stirringAfter 15 minutes of stirring at 0° C.
  4. addition6N aqueous sodium hydroxide (1.24 mL) was added dropwise
  5. stirringThe reaction mixture was stirred for 1.5 h at 0° C.
  6. concentrationconcentrated in vacuo
  7. additionWater (10 mL) was added to the residue
  8. extractionthe solution extracted with ethyl acetate (3×15 mL)
  9. dry with materialthe combined organic layers dried over magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0efd3a38a7d34885bc3f8c1e0ccd7c37
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Linked notes

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