2,6-Lutidine → HCID 90093713, compound

HRID 1753075Notes

Reaction equation

HRID 1753075 reaction equation
[F:1][C:2]1[C:3]2[N:10]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])[CH:9]=[C:8]([I:16])[C:4]=2[CH:5]=[N:6][CH:7]=1.N1C(C)=CC=CC=1C.[CH3:25][C:26]([Si:29](OS(C(F)(F)F)(=O)=O)([CH3:31])[CH3:30])([CH3:28])[CH3:27]>C(Cl)Cl>[C:26]([Si:29]([CH3:31])([CH3:30])[O:13][CH2:12][C:11]([N:10]1[C:3]2[C:2]([F:1])=[CH:7][N:6]=[CH:5][C:4]=2[C:8]([I:16])=[CH:9]1)([CH3:14])[CH3:15])([CH3:28])([CH3:27])[CH3:25]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 90093910HCID 90093910, compound

Product 1

HCID 90093713HCID 90093713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(7-fluoro-3-iodo-pyrrolo[3,2-c]pyridin-1-yl)-2-methyl-propan-1-ol (Preparation 72, 4.5 gm, 13.47 mmol) in DCM (90 mL) were added 2,6-lutidine (3.91 mL, 33.65 mmol) and tert-butyl dimethylsilyl trifluoromethanesulfonate (4.62 gm, 17.51 mmol) at 0° C. The resulting mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was diluted with DCM. The organic layer was washed with water, brine, dried over sodium sulphate, and evaporated in vacuo. The crude material was purified by silica gel column chromatography eluting with 10-12% EtOAc in Hexane to afford the title compound as off white solid (45%, 2.7 g).

Workup

  1. washThe organic layer was washed with water, brine
  2. dry with materialdried over sodium sulphate
  3. customevaporated in vacuo
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with 10-12% EtOAc in Hexane

Sources & evidence

ORD record
ord-9e8acbcaeb5941dda7cdfe2b8f0a4278
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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