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

HRID 592251노트

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HRID 592251 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
98 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-298737c17fd94fb5831160e996eede4a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238646B2

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