Imidazole → 1-benzyl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-pyrrolo[3,2-b]pyridine

HRID 628293Notes

Reaction equation

HRID 628293 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[CH2:14]([N:21]1[C:29]2[C:24](=[N:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[CH:23]=[C:22]1[CH2:31][OH:32])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[CH2:14]([N:21]1[C:29]2[C:24](=[N:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[CH:23]=[C:22]1[CH2:31][O:32][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 118159445(1-benzyl-5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)methanol

Product 1

HCID 1235320351-benzyl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-pyrrolo[3,2-b]pyridineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyldimethylsilyl chloride (0.12 g, 0.81 mmol) and 1H-imidazole (60. mg, 0.88 mmol) were added to a solution of (1-benzyl-5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)methanol (0.20 g, 0.73 mmol, from Step 2) in DCM (10 mL) After stirring for 4 hours, additional tert-butyldimethylsilyl chloride (33 mg, 0.22 mmol) and 1H-imidazole (15 mg, 0.22 mmol) were added and the reaction was continued for one hour. The mixture was filtered and the filtrate was concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-10% EtOAc in hexanes to afford a white solid (0.26 g, 92%).

Workup

  1. waitthe reaction was continued for one hour
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe product was purified by flash chromatography
  5. washeluting with a gradient from 0-10% EtOAc in hexanes

Sources & evidence

ORD record
ord-fb24d47e80674deb96dd2b23453afd44
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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