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Ethyl Bromide → methyl 4-(3-amino-6-(1-ethyl-1H-pyrazol-4-yl)pyrazin-2-yl)-2-fluorobenzoate

HRID 596098
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HRID 596098 반응식
[NH2:1][C:2]1[C:3]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([F:23])[CH:14]=2)=[N:4][C:5]([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH3:32]>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([F:23])[CH:14]=2)=[N:4][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:31][CH3:32])[CH:12]=2)=[CH:6][N:7]=1
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HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 118045485methyl 4-(3-amino-6-(1H-pyrazol-4-yl) pyrazin-2-yl)-2-fluorobenzoate

생성물 1

HCID 118045915methyl 4-(3-amino-6-(1-ethyl-1H-pyrazol-4-yl)pyrazin-2-yl)-2-fluorobenzoate수율 63.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To methyl 4-(3-amino-6-(1H-pyrazol-4-yl) pyrazin-2-yl)-2-fluorobenzoate (45 mg, 0.115 mmol) in DMF (2 mL) was added potassium carbonate (47.6 mg, 0.345 mmol), followed by bromoethane (0.017 mL, 0.230 mmol). The reaction mixture was stirred at room temperature for 48 h. The reaction mixtures was partitioned between ethylacetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, evaporated and purified by flash chromatography eluting with 0-60% of EtOAc (contains 10% of MeOH)/heptane to yield the desired product (25 mg, 64%, 80% purity). LCMS (m/z): 342.0 (MH+), 0.73 min.

후처리

  1. customThe reaction mixtures
  2. customwas partitioned between ethylacetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by flash chromatography
  9. washeluting with 0-60% of EtOAc (contains 10% of MeOH)/heptane

출처 및 근거

ORD 기록
ord-18eef34053d94b1e9a4a2f2bb2e3e98e
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242996B2

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