Water → HCID 68630708, compound

HRID 1931505Notes

Reaction equation

[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16](Br)[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.O.[CH3:23][N:24](C=O)C>[C-]#N.[Zn+2].[C-]#N.[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@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:23]#[N:24])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of (R)-indan-1-yl-(6-bromo-quinolin-2-yl)-amine (1.14 g, 3.36 mmol), zinc cyanide (434 mg, 3.7 mmol) and tetrakis-(triphenylphosphine)-palladium (388 mg, 0.34 mmol) in DMF (12 ml) was heated at 160° C. for 15 min in a microwave reactor. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (2×50 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (diethyl ether/heptane) to yield 2-((R)-indan-1-ylamino)-quinoline-6-carbonitrile as light yellow solid (310 mg, 32%).

Workup

extractionextracted with ethyl acetate (3×100 ml)
washThe combined organic layers were washed with brine (2×50 ml)
dry with materialdried (MgSO4)
customevaporated
customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (diethyl ether/heptane)

Sources & evidence

ORD record: ord-f76e5fa4f0c84972af31069659f86cc0
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188284B2

Reaction notes

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