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Isopropylamine → HCID 136344026, compound

HRID 1050770
Notes
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Reaction equation

HRID 1050770 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:14][S:13][C:9]2=[C:10](Br)[N:11]=1)=[O:5])[CH3:2].[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26].C(N)(C)C>C1COCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])=[C:8]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[N:14][S:13][C:9]2=[C:10]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])[N:11]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 6363IsopropylamineHCID 66111TrimethylsilylacetyleneHCID 136344041HCID 136344041, compound

Product 1

HCID 136344026HCID 136344026, compoundYield 37.7%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418476
HCID 178418476, compound
Catalyst
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-Bromo-3-(4-chloro-phenyl)-4-hydroxy-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (152.5 mg, 0.369 mmol) in THF (5.2 mL) were added Trimethylsilylacetylene (0.105 mL, 0.738 mmol), PdCl2(PPh3)2 (51.8 mg, 0.0738 mmol), CuI (28.1 mg, 0.147 mmol) and isopropylamine (0.32 mL, 2.28 mmol). The reaction mixture was refluxed for 16 h. After cooling to rt, the mixture was diluted with EtOAc (20 mL), and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography on silica gel. Elution with 0-20% EtOAc/CH2Cl2, gave the desired product (60 mg) as white solid: MS (m/z) 431.1 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by flash chromatography on silica gel
  5. washElution with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-540a9597df9d4b48926f199142a4ec67
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09387200B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes