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Water → Methyl 4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

HRID 516052
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HRID 516052 반응식
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:14]([N:16]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[N:17]1)[CH3:15].C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.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.CCOC(C)=O>[C:12]([C:8]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([C:19]2[CH:18]=[N:17][N:16]([CH2:14][CH3:15])[CH:20]=2)[N:11]=[CH:10][CH:9]=1)#[N:13]
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8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 113790451-Ethyl-1H-pyrazole-4-boronic acid, pinacol esterHCID 58317566Methyl 2-chloro-4-cyanonicotinate

생성물 1

HCID 58317527Methyl 4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate수율 114.4%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A mixture of methyl 2-chloro-4-cyanonicotinate (207 mg, 1.053 mmol), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (201 mg, 0.905 mmol) and tetrakis(triphenylphosphine)palladium(0) (122 mg, 0.105 mmol) in DME (2 mL), and saturated aq Na2CO3 (2 mL) was stirred at 80° C. for 3 h under N2 atmosphere. Water and EtOAc were subsequently added. The organic phase was washed with H2O and brine, dried over MgSO4, and evaporated to yield the title compound (265.3 mg, 98%). [M+H] calc'd for C13H12N4O2, 257; found, 257.

후처리

  1. washThe organic phase was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. customevaporated

출처 및 근거

ORD 기록
ord-a0befa56f5224bb888a2ef6dbeb91f95
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108970B2

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