Diethyl Ether → HCID 58730937, compound

HRID 1994199Notes

Reaction equation

HRID 1994199 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([Si](C(C)(C)C)(C)C)[C:5]2=[N:6][CH:7]=1.[C:18]([Li])([CH3:21])(C)C.[CH3:23][CH2:24][CH2:25][CH2:26][CH3:27].C[CH2:29][O:30]CC>>[NH:8]1[C:5]2=[N:6][CH:7]=[C:2]([CH:29]([C:25]3[CH:26]=[CH:27][C:18]([CH3:21])=[CH:23][CH:24]=3)[OH:30])[CH:3]=[C:4]2[CH2:10][CH2:9]1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8003PentaneHCID 587309295-Bromo-1-(tert-butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 58730937HCID 58730937, compoundYield 19%

Procedure

To a stirred and cooled (−78° C.) solution of the bromide 4 (100 mg, 0.32 mmol) in Et2O (1.8 mL) was added dropwise 1.5 M solution of tert-butyllithium in pentane (0.45 mL, 0.67 mmol). The mixture was stirred for an additional 0.6 h at −78° C., p-tolylaldehyde (0.04 mL, 0.32 mmol) was added, and the mixture slowly allowed to warm to r.t. After 18 h the mixture was partitioned between AcOEt-brine. The aqueous layer was extracted with AcOEt (2×). The combined organic solutions were dried (MgSO4), concentrated, and the residue was purified by PTLC with CH2Cl2:MeOH=95:5 as eluent to afford alcohol 19 (15 mg, 19%) as a white solid. 1H NMR (400 MHz; CDCl3) δ 2.34 (s, 3H), 5.99 (s, 1H), 6.45 (d, J=3.5 Hz, 1H), 7.16 (d, J=7.8 Hz, 2H), 7.30-7.32 (m, 3H), 7.93 (d, J=1.8 Hz, 1H), 8.32 (d, J=2.0 Hz, 1H) and 9.77 (br s, NH).

Workup

  1. stirringThe mixture was stirred for an additional 0.6 h at −78° C.
  2. customAfter 18 h the mixture was partitioned between AcOEt-brine
  3. extractionThe aqueous layer was extracted with AcOEt (2×)
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was purified by PTLC with CH2Cl2

Sources & evidence

ORD record
ord-4144459b87cf4e109bc640b09fc5fd93
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

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