Pyridine → HCID 89676875, compound

HRID 2207046Notes

Reaction equation

HRID 2207046 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].N1C=CC=CC=1.[Br:14][C:15]1[C:24]([CH:25]([O:28][C:29]([CH3:35])([CH3:34])[C:30]([F:33])([F:32])[F:31])[CH2:26][OH:27])=[C:23]([CH3:36])[CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2>C(Cl)Cl>[C:3]([O:27][CH2:26][CH:25]([C:24]1[C:15]([Br:14])=[C:16]2[C:21](=[CH:22][C:23]=1[CH3:36])[N:20]=[CH:19][CH:18]=[CH:17]2)[O:28][C:29]([CH3:35])([CH3:34])[C:30]([F:31])([F:33])[F:32])(=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 89676571HCID 89676571, compound

Product 1

HCID 89676875HCID 89676875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of trimethylacetyl chloride (19 μL, 0.15 mmol) in pyridine (0.4 mL, 4.95 mmol) was added 2-(5-bromo-7-methylquinolin-6-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethanol (29.8 mg, 0.08 mmol) in CH2Cl2 (0.4 mL) at 0° C. The reaction mixture was allowed to warm to room temperature overnight. The mixture was quenched with water and concentrated and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to give 2-(5-bromo-7-methylquinolin-6-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethyl pivalate. LCMS-ESI+ (m/z): [M+H]+ calc'd for C21H26BrF3NO3: 476.11; Found: 476.2.

Workup

  1. customThe mixture was quenched with water
  2. concentrationconcentrated
  3. custompurified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d2cb4cfe8e6c4d3d8e492a4ca20fda8c
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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