Lithium Chloride → HCID 21956523, 화합물

HRID 2213098노트

반응식

HRID 2213098 반응식
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.FC(F)(F)S(O[C:26]1[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][C:27]=1[O:34][CH3:35])(=O)=O.[Cl-].[Li+]>CN(C=O)C.C(OCC)C.O.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>[CH3:35][O:34][C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][C:26]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[C:32]#[N:33]

참가 물질

8

반응물 3

HCID 433294Lithium ChlorideHCID 6077842-(Tributylstannyl)pyridineHCID 166592584-Cyano-2-methoxyphenyl trifluoromethanesulfonate

생성물 1

HCID 21956523HCID 21956523, 화합물

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A solution of 2-(tributylstannyl)pyridine (18 g of 80% pure, 39.2 mmol) and 4-cyano-2-methoxyphenyl trifluoromethanesulfonate (9.2 g, 32.7 mmol) were dissolved in DMF (65 mL) and treated with lithium chloride (1.39 g, 32.7 mmol) and Pd(PPh3)4 (1.9 g, 1.6 mmol), then degassed by bubbling argon through the solution for 15 min. The reaction mixture was heated to 100° C. while under an atmosphere of argon for 12 h. The cooled reaction mixture was diluted with diethyl ether (100 mL) and water (100 mL). The organic layer was separated and washed with a 1M solution of sodium hydroxide (50 mL) and brine (50 mL), then dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 1:1) to afford 3-methyoxy-4-pyridin-2-ylbenzonitrile.

후처리

  1. customdegassed
  2. customby bubbling argon through the solution for 15 min
  3. customThe cooled reaction mixture
  4. customThe organic layer was separated
  5. washwashed with a 1M solution of sodium hydroxide (50 mL) and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 1:1)

출처 및 근거

ORD 기록
ord-6f58c5203533400ebf11ac98e78b3bd2
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105533B2

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