Potassium Carbonate → HCID 86679135、化合物

HRID 1774757ノート

反応式

HRID 1774757 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24](Br)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24]([O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 5995293-Bromo-5-hydroxypyridineHCID 53415291tert-Butyl 3-bromoazetidine-1-carboxylate

生成物 1

HCID 86679135HCID 86679135、化合物収率 100%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of 5-bromopyridin-3-ol (0.285 g, 1.64 mmol) in DMF (2.5 mL) was added K2CO3 (0.453 g, 3.28 mmol), followed by 3-bromo-azetidine-1-carboxylic acid tert-butyl ester (0.425 g, 1.8 mmol) in DMF (0.5 mL) and the reaction mixture was heated to 60° C. and stirred over night. The reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 solution (10 mL) and the aqueous layer was extracted EtOAc (2×20 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 50% EtOAc-heptane gradient to give the title compound (0.539 g, 100%) as a colorless crystalline solid. MS: 329.1 (M+H+).

後処理

  1. extractionthe aqueous layer was extracted EtOAc (2×20 mL)
  2. washCombined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel flash chromatography
  7. washeluting with a 0 to 50% EtOAc-heptane gradient

出典と根拠

ORDレコード
ord-f46151f629f04261814d12a71ad0993b
出典データセット
uspto-grants-2016_02
特許番号
US09260408B2

反応ノート

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