Dimethylformamide → HCID 90386955, compound

HRID 1476805Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([CH2:12][OH:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:48][N:49](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:13][CH2:12][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([C:48]#[N:49])[N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of (3-chloroisoquinolin-1-yl)methanol (1.0 g, 5.17 mmol), zinc cyanide (672 mg, 5.68 mmol), Pd2(dba)3 (190 mg, 0.21 mmol), XPhos (241 mg, 0.52 mmol) in DMF (15 mL) was heated at 150° C. for 1 hour under a nitrogen atmosphere in a microwave reactor. The reaction mixture was subsequently diluted with water and extracted with EtOAc. The organic layer was separated and dried over Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel chromatography eluting with petroleum ether and EtOAc (4:1) to give the title compound as a yellow solid (330 mg, 34%). ESI-MS m/z [M+H]+ 185.1.

Workup

extractionextracted with EtOAc
customThe organic layer was separated
dry with materialdried over Na2SO4
customthe solvent was evaporated under reduced pressure
customThe crude product was purified by silica gel chromatography
washeluting with petroleum ether and EtOAc (4:1)

Sources & evidence

ORD record: ord-71c357411c464b798612e244b09bc2a8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09402841B2

Reaction notes

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