Sodium Hydroxide → {3-hydroxy-1-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile

HRID 1426332Notes

Reaction equation

HRID 1426332 reaction equation
[Si]([O:18][CH:19]1[CH2:22][C:21]([CH2:45][C:46]#[N:47])([N:23]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]4[N:34]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:35]=[CH:36][C:29]=34)[CH:25]=[N:24]2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[OH-].[Na+]>O.C(O)C>[OH:18][CH:19]1[CH2:22][C:21]([CH2:45][C:46]#[N:47])([N:23]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]4[N:34]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:44])[CH3:43])[CH:35]=[CH:36][C:29]=34)[CH:25]=[N:24]2)[CH2:20]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67954160{3-{[tert-Butyl(diphenyl)silyl]oxy}-1-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile

Product 1

HCID 67968346{3-hydroxy-1-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

To {3-{[tert-butyl(diphenyl)silyl]oxy}-1-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile (2.0 g, 3.0 mmol, a mixture of diastereomers from Step A) ethanol (82 mL) was added 5.0M sodium hydroxide in water (9 mL, 50 mmol). The reaction was stirred overnight. The reaction mixture was diluted with water and ethanol was removed in vacuo. The aqueous mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with water, then brine, dried over sodium sulfate, decanted and concentrated. The product, as a mixture of diastereomers, was used without further purification in Step C. LCMS (M+H)+: 424.2.

Workup

  1. customwas removed in vacuo
  2. extractionThe aqueous mixture was extracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated
  7. additionThe product, as a mixture of diastereomers
  8. customwas used without further purification in Step C

Sources & evidence

ORD record
ord-36b43654c5b84a329721c0a31c75e2c4
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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