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

HRID 2079973
Notes
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Reaction equation

HRID 2079973 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4953d15a6a11419ea17fd687216582df
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932272B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes