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Water → 2-Amino-6-(1-ethoxyvinyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2079973
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HRID 2079973 반응식
[CH2:1]([O:3][C:4]([Sn](CCCC)(CCCC)CCCC)=[CH2:5])[CH3:2].[NH2:19][C:20]1[N:41]=[C:40](Cl)[CH:39]=[CH:38][C:21]=1[C:22]([NH:24][CH2:25][C:26]1[S:27][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:29][CH:30]=1)=[O:23].C1(C)C(C)=CC=CC=1.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.C(OCC)(=O)C>[NH2:19][C:20]1[N:41]=[C:40]([C:4]([O:3][CH2:1][CH3:2])=[CH2:5])[CH:39]=[CH:38][C:21]=1[C:22]([NH:24][CH2:25][C:26]1[S:27][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:29][CH:30]=1)=[O:23]
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7

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HCID 962WaterHCID 7237O-XyleneHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 231304982-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

생성물 1

HCID 231303892-Amino-6-(1-ethoxyvinyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide수율 82.6%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8857Ethyl Acetate용매

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온도
130 °C

실험 절차

1-Ethoxyvinyl(tri-n-butyl)tin (0.47 mL, 1.4 mmol) was added to a mixture of 2-amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide (170 mg, 0.46 mmol) described in Preparation Example A+-11, tetrakis(triphenylphosphine)palladium(0) (54 mg, 0.046 mmol) and xylene (5 mL), and the solution was stirred for 2.5 hours at 130° C. After cooling, water and ethyl acetate were added to the reaction solution for extraction, and the solution was washed with brine. The solvent was evaporated in vacuo, then, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=2:1), and the title compound (150 mg, 0.38 mmol, 82%) was obtained as a pale yellow solid.

후처리

  1. temperatureAfter cooling
  2. washthe solution was washed with brine
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-4953d15a6a11419ea17fd687216582df
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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