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Ethynylcyclobutane → HCID 57908178, compound

HRID 1044015
Notes
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Reaction equation

HRID 1044015 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4](I)[CH:3]=1.[C:17]([CH:19]1[CH2:22][CH2:21][CH2:20]1)#[CH:18]>CCN(CC)CC.C1COCC1.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>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([C:18]#[C:17][CH:19]2[CH2:22][CH2:21][CH2:20]2)[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 2

HCID 142749EthynylcyclobutaneHCID 53415320tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

Product 1

HCID 57908178HCID 57908178, compoundYield 60%

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476
HCID 178418476, compound
Catalyst
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

To the solution of tert-butyl 6-chloro-4-iodopyridin-3-ylcarbamate (7.0 g, 19.8 mmol) in Et3N (100 mL) was added the solution of ethynylcyclobutane in THF (prepared in step a), Pd(PPh3)2Cl2 (1.8 g, 2.1 mmol) and CuI (400 mg, 2.1 mmol). The reaction mixture was stirred at 25° C. for 16 h. The mixture was diluted with water and extracted with dichloromethane (3×100 mL). The extract was washed with brine, dried, concentrated in vacuo and purified by chromatography on silica gel (5-10% ethyl acetate in petroleum ether as eluant) to afford tert-butyl 6-chloro-4-(cyclobutylethynyl)pyridin-3-ylcarbamate (3.6 g, 60% yield). 1H NMR (300 MHz, CDCl3) δ: 9.11 (br, s, 1H), 7.22 (s 1H), 6.97 (s, 1H), 3.39-3.25 (m, 1H), 2.48-1.98 (m, 6H), 1.52 (s, 9H).

Workup

  1. extractionextracted with dichloromethane (3×100 mL)
  2. washThe extract was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography on silica gel (5-10% ethyl acetate in petroleum ether as eluant)

Sources & evidence

ORD record
ord-d78b6778637f40f4962bf3956da92f55
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563573B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes