Methanol → HCID 66621285, compound

HRID 415159Notes

Reaction equation

HRID 415159 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:5]=[CH:4][C:3]=1[C:13]1[O:14][C:15]2[C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1.S(Cl)(Cl)=O.[CH3:29]O>>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:5]=[CH:4][C:3]=1[C:13]1[O:14][C:15]2[C:21]([C:22]([O:24][CH3:29])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 66620465HCID 66620465, compound

Product 1

HCID 66621285HCID 66621285, compoundYield 38%

Conditions

Temperature
70 °C

Procedure

2-(2-Fluoro-4-(pyrrolidin-2-yl)phenyl)benzo[d]oxazole-7-carboxylic acid (500 mg, 1.53 mmol) was dissolved in methanol (20 mL) at −5° C.-0° C., thionyl chloride (0.2 mL, 2.40 mmol) was added dropwise. The mixture was heated at 70° C. for 3 h., then evaporated and the residue was adjusted to pH=9 by NaHCO3, and extracted with ethyl acetate. The organic layer was separated and washed with brine, dried over anhydrous sodium sulfate and evaporated to give methyl 2-(2-fluoro-4-(pyrrolidin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate (200 mg, yield 38%) as white solid. LC-MS (ESI) m/z: 341 (M+1)+.

Workup

  1. customevaporated
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-3680b0c74f9044889eb278ae12195aa6
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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