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Dichloromethane → 2-(5-Ethylisochroman-1-yl)-4,5-dihydro-1H-imidazole

HRID 1771411
Notes
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Reaction equation

HRID 1771411 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]1[NH:13][CH2:14][CH2:15][N:16]=1.[CH2:17](B(O)O)[CH3:18].C(Cl)Cl.[F-].[Cs+]>CN(C=O)C.O1CCOCC1>[CH2:17]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]1[NH:13][CH2:14][CH2:15][N:16]=1)[CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 25953Cesium fluorideHCID 521157Ethylboronic acidHCID 717669082-(5-bromoisochroman-1-yl)-4,5-dihydro-1H-imidazole

Product 1

HCID 717669102-(5-Ethylisochroman-1-yl)-4,5-dihydro-1H-imidazole

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-(5-bromoisochroman-1-yl)-4,5-dihydro-1H-imidazole (100 mg), ethylboronic acid (56.2 mg), (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II), complex with CH2Cl2 (1:1) (13 mg) and CsF (108 mg) was added dioxane (4 ml) and DMF (1 ml). The mixture was degassed with N2 and heated in a microwave oven for 30 min at 100° C. and 30 min at 150° C. The title compound was purified by separation methods J and G. (Yield 6.1 mg).

Workup

  1. customThe mixture was degassed with N2
  2. customThe title compound was purified by separation methods J and G

Sources & evidence

ORD record
ord-5a42abff884a4d3f8c4eeb9c278a0cda
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249127B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes