1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzoic acid

HRID 883030ノート

反応式

HRID 883030 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:17]([CH:18]=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CC1C=CC(S([CH2:30][N+:31]#[C-:32])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1>COCCOC>[F:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:17]([C:18]3[O:19][CH:32]=[N:31][CH:30]=3)=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 161915Tosylmethyl isocyanideHCID 866237872-Fluoro-5-(3-formylpyridin-2-yloxy)benzoic acid

生成物 1

HCID 691660742-Fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzoic acid

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

To 2-fluoro-5-(3-formylpyridin-2-yloxy)benzoic acid (230 mg, 0.881 mmol) and TosMIC (172 mg, 0.881 mmol) in DME (8.0 mL) was added DBU (0.29 mL, 1.9 mmol). The mixture was heated to 85° C. for 2.5 hours in a sealed tube. After concentrated, the residue was diluted with saturated sodium carbonate and extracted with EtOAc. The aqueous layer was acidified with TFA (pH˜3) and the resulting solid was filtered and dried to yield 2-fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzoic acid as a beige solid. MS m/z=301 [M+1]+. Calc'd for C15H9FN2O4: 300.25.

後処理

  1. concentrationAfter concentrated
  2. additionthe residue was diluted with saturated sodium carbonate
  3. extractionextracted with EtOAc
  4. filtrationthe resulting solid was filtered
  5. customdried

出典と根拠

ORDレコード
ord-09f979db78754641836bc59f977a8fdd
出典データセット
uspto-grants-2012_08
特許番号
US08236823B2

反応ノート

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