Triethylamine → HCID 118150078, compound

HRID 634371Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[O:4][C:3]=1[CH:13]([OH:15])[CH3:14].[CH3:16][N:17]([CH2:28][C:29]#[CH:30])[C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.CCCCCCC>CN(C=O)C.[Cu]I.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.CCOC(C)=O>[OH:15][CH:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:11]([C:2]=1[C:30]#[C:29][CH2:28][N:17]([CH3:16])[C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of 4-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate A2, 2.65 g, 9.84 mmol) in dry DMF (30 ml), benzyl methyl(prop-2-yn-1-yl)carbamate (Intermediate G22, 4 g, 19.68 mmol), copper(I) iodide (0.562 g, 2.95 mmol), tetrakis(triphenylphosphine)palladium(0) (1.946 ml, 1.476 mmol), benzyl methyl(prop-2-yn-1-yl)carbamate (4 g, 19.68 mmol) and triethylamine (4.04 ml, 29.5 mmol) were added. The resulting suspension was heated to 95° C. overnight. Then, solvent was removed under reduced pressure. The product was purified by Biotage Si 10 g with a gradient of heptane and EtOAc affording the title compound (3.524 g, 9.00 mmol, 91% yield) a yellowish oil.

Workup

customThen, solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-f5087b2c534045f7a034870853cbc078
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

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