HCID 123309962, compound → 1-(tert-butyl)-3-((5-chloro-3-(hydroxymethyl)pyridin-2-yl)methyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

HRID 706402Notes

Reaction equation

HRID 706402 reaction equation
[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]([CH2:14][C:15]2[C:20]([CH2:21][O:22][Si](C(C)C)(C(C)C)C(C)C)=[CH:19][C:18]([Cl:33])=[CH:17][N:16]=2)[C:6]1=[O:34])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]([CH2:14][C:15]2[C:20]([CH2:21][OH:22])=[CH:19][C:18]([Cl:33])=[CH:17][N:16]=2)[C:6]1=[O:34])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 123309962HCID 123309962, compound

Product 1

HCID 717382771-(tert-butyl)-3-((5-chloro-3-(hydroxymethyl)pyridin-2-yl)methyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-oneYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 69 (max 60.7 mmol) in THF (50 mL) obtained from the previous step was degassed with vacuum/flush N2, cooled below 5° C. followed by charged TBAF (79 ml, 1.0 N in THF). The reaction aged at room temperature for 1 h 20 min, cooled below 10° C., quenched with water (100 ml), and diluted with AcOEt (200 mL). Aqueous layer was extracted with AcOEt (100 mL). The combined organic layer was dried with MgSO4, filtered, concentrated and purified by silica gel column (50 to 100% AcOEt/hexane) to give 56 (16.3 g, 78% from 65) as a solid.

Workup

  1. customwas degassed with vacuum/flush N2
  2. temperaturecooled below 5° C.
  3. additionby charged TBAF (79 ml, 1.0 N in THF)
  4. temperaturecooled below 10° C.
  5. customquenched with water (100 ml)
  6. additiondiluted with AcOEt (200 mL)
  7. extractionAqueous layer was extracted with AcOEt (100 mL)
  8. dry with materialThe combined organic layer was dried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by silica gel column (50 to 100% AcOEt/hexane)

Sources & evidence

ORD record
ord-f1355ae620ae49ab9cd78726c9db3a3a
Source dataset
uspto-grants-2015_11
Patent number
US09174989B2

Reaction notes

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