Acrylamide → HCID 18172407, compound

HRID 397099Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[CH2:11][CH2:10][N:9]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:32]([NH2:36])(=[O:35])[CH:33]=[CH2:34]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[CH:8]([C:5]1[CH:4]=[CH:3][C:2](/[CH:34]=[CH:33]/[C:32]([NH2:36])=[O:35])=[CH:7][CH:6]=1)[N:9]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10][CH2:11]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 1-(4-iodo-phenyl)-2-phenyl-1,2,3,4-tetrahydroisoquinolin-6-ol (0.100 g, 0.234 mmol), triethylamine (0.163 ml, 1.17 mmol), and acrylamide (0.082 g, 0.351 mmol) in DMF (2 ml), under an atmosphere of N2, was added Pd(PPh3)4 (0.014 g, 0.012 mmol). The solution was heated to 100° C. overnight, then cooled to RT and diluted with water (20 ml). The aqueous mixture was extracted with EtOAc (3×10 ml). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. The residue was subjected to flash chromatography (SiO2, 5% MeOH/CH2Cl2) to give the desired product (0.030 g, 0.089 mmol, 35% yield).

Workup

temperaturecooled to RT
extractionThe aqueous mixture was extracted with EtOAc (3×10 ml)
dry with materialThe combined organics were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-72cb812f5eda474abeee39ad75b61188
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608203B2

Reaction notes

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