Thiomorpholine → 4-(5-Bromopyridin-2-yl)thiomorpholine

HRID 1036296ノート

反応式

HRID 1036296 の反応式
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[CH:10][C:11](I)=[N:12][CH:13]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([N:1]2[CH2:6][CH2:5][S:4][CH2:3][CH2:2]2)=[N:12][CH:13]=1

参加物

7

反応物 4

HCID 67164ThiomorpholineHCID 5936905-Bromo-2-iodopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178418730sodium 2-methylpropan-2-olate

生成物 1

HCID 177499624-(5-Bromopyridin-2-yl)thiomorpholine

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
98 °C

実験手順

A mixture of thiomorpholine (1.03 g, 10.0 mmol), 5-bromo-2-iodopyridine (3.69 g, 13 mmol), Pd2(dba)3 (200 mg, 0.2 mmol), xantphos (510 mg, 0.6 mmol) and t-BuONa (1.44 g, 15 mmol) in toluene (50 ml) was stirred under argon at 98° C. for 3 hours. After cooled to room temperature, the mixture was filtered through celite and washed with ethyl acetate. The filtrate was evaporated and the residue was subjected to silica gel column chromatography with 0-5% ethyl acetate in hexanes as eluent to give 4-(5-bromopyridin-2-yl)thiomorpholine 219-2 as solid.

後処理

  1. temperatureAfter cooled to room temperature
  2. filtrationthe mixture was filtered through celite
  3. washwashed with ethyl acetate
  4. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-02e3e9bd3373460cad3ec8a61014d912
出典データセット
uspto-grants-2013_10
特許番号
US08546396B2

反応ノート

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