Trimethylsilylacetylene → 2-(5-Ethynylisochroman-1-yl)-4,5-dihydro-1H-imidazole

HRID 1771415Notes

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.[C:17]([Si](C)(C)C)#[CH:18]>CCN(CC)CC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C: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)#[CH:18]

Participants

Conditions

Temperature: 120 °C

Procedure

To a degassed solution of 2-(5-bromoisochroman-1-yl)-4,5-dihydro-1H-imidazole (300 mg) in Et3N (10 ml) and ethynyltrimethylsilane (210 mg) was added tetrakis(triphenylphosphine)-palladium (37 mg). The mixture was degassed with N2 and heated in a microwave oven for 60 min at 120° C. The reaction mixture was concentrated under vacuum and purified by separation method K. K2CO3 was added to the reaction crude (in MeOH) and the mixture was stirred 4 h at it. The title compound was isolated by a separation method G. (Yield 6.2 mg).

Workup

customThe mixture was degassed with N2
concentrationThe reaction mixture was concentrated under vacuum
custompurified by separation method K
additionK2CO3 was added to the reaction crude (in MeOH)

Sources & evidence

ORD record: ord-5de70b8108b442bf833bba75367ebcb6
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249127B2

Reaction notes

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