Sodium Carbonate → HCID 57598244、化合物

HRID 2205524ノート

反応式

HRID 2205524 の反応式
Br[C:2]1[S:6][C:5]([CH2:7][OH:8])=[N:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[S:6][C:5]([CH2:7][OH:8])=[N:4][N:3]=2)=[CH:12][CH:11]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 63384078(5-Bromo-1,3,4-thiadiazol-2-yl)methanol

生成物 1

HCID 57598244HCID 57598244、化合物収率 65.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of (5-bromo-1,3,4-thiadiazol-2-yl)methanol (1.2 g, 6.153 mmol) in toluene (40 mL) and ethanol (40 mL) was added 4-fluorophenyl boronic acid (1.026 g, 7.384 mmol) and 2 M solution of aqueous Na2CO3. The reaction mixture was degassed with argon, Pd(PPh3)4 (0.354 g, 0.355 mmol) was added, the reaction mixture again degassed with argon for 10 min, and the mixture heated to 100° C. for 2 h. The reaction mixture was evaporated under vacuum to remove the ethanol, diluted with water (50 mL), extracted with ethyl acetate (200 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was purified by Biotage IsoleraOne® column (using 30% ethyl acetate and hexane) to give (5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)methanol as pale yellow solid (0.85 g, 65% yield); LC-MS m/z calculated for [M+H]+ 211.03. found 211.1.

後処理

  1. additionwas added
  2. customthe reaction mixture again degassed with argon for 10 min
  3. customThe reaction mixture was evaporated under vacuum
  4. customto remove the ethanol
  5. additiondiluted with water (50 mL)
  6. extractionextracted with ethyl acetate (200 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto obtain crude product
  11. customThe crude product was purified by Biotage IsoleraOne® column (using 30% ethyl acetate and hexane)

出典と根拠

ORDレコード
ord-904e086fa6ae45b6ac3ef80edad43c23
出典データセット
uspto-grants-2016_06
特許番号
US09371316B2

反応ノート

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