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Ammonia → 4-Benzyl-5-bromo-2-(3-hydroxy-1-butynyl)pyridine

HRID 1359390
ノート
印刷プレビュー

反応式

HRID 1359390 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([Br:20])=[CH:9][N:8]=1)(=O)=O.[CH:23]#[C:24][CH:25]([OH:27])[CH3:26].C(N(CC)CC)C.N>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.CN(C)C=O>[CH2:13]([C:11]1[C:10]([Br:20])=[CH:9][N:8]=[C:7]([C:23]#[C:24][CH:25]([OH:27])[CH3:26])[CH:12]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 181821814-Benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate

生成物 1

HCID 181823824-Benzyl-5-bromo-2-(3-hydroxy-1-butynyl)pyridine収率 79%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6228Dimethylformamide溶媒

実験手順

650 mg of 4-benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate (Production Example 1), 115 mg of 1-butyne-3-ol, 100 mg of tetrakis(triphenylphosphine)palladium(0), 30 mg of cuprous iodide and 1 ml of triethylamine were mixed with 5 ml of N,N-dimethylformamide, followed by stirring for one hour in an oil bath kept at 60° C. After cooling as it was, aqueous ammonia was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with brine and then evaporated. The residue was subjected to silica gel column chromatography and eluted with 30% ethyl acetate/hexane, to give 410 mg of the target compound.

後処理

  1. customkept at 60° C
  2. temperatureAfter cooling as it
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. customevaporated
  6. washeluted with 30% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-1dd072695ddb49ac9e1f3f4994eb8c26
出典データセット
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06599917B1

反応ノート

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