Triethylamine → [7-(5,6-Dihydro-4H-pyran-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl ester

HRID 1582161Notes

Reaction equation

HRID 1582161 reaction equation
[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S:6][C:7]2[C:13](I)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.C([Sn](CCCC)(CCCC)[C:23]1[O:24][CH2:25][CH2:26][CH2:27][CH:28]=1)CCC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(N(CC)CC)C>O1CCOCC1.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]>[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S:6][C:7]2[C:13]([C:23]3[O:24][CH2:25][CH2:26][CH2:27][CH:28]=3)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 521585Tris(furan-2-yl)phosphaneHCID 4216837tributyl(3,4-dihydro-2H-pyran-6-yl)stannaneHCID 60117385(7-Iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

Product 1

HCID 86588851[7-(5,6-Dihydro-4H-pyran-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

From (7-iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester with tributyl-(5,6-dihydro-4H-pyran-2-yl)-stannane, bis(dibenzylideneacetone)palladium, trifurylphosphine and triethylamine in dioxane. ES-MS m/e (%): 321 (M+H+, 100).

Sources & evidence

ORD record
ord-90ce4a8777db43cda6ec58b635fd1687
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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