HCID 71256713, compound → HCID 71256586, compound

HRID 1627730Notes

Reaction equation

[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([O-:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].C([N+](CCCC)(CCCC)CCCC)CCC.I[CH2:31]/[CH:32]=[CH:33]/[B:34]1[O:38][C:37]([CH3:40])([CH3:39])[C:36]([CH3:42])([CH3:41])[O:35]1>ClCCl>[CH3:39][C:37]1([CH3:40])[C:36]([CH3:41])([CH3:42])[O:35][B:34](/[CH:33]=[CH:32]/[CH2:31][O:12][C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]=3[CH:11]=2)[O:38]1

Participants

Conditions

Temperature: 80 °C

Procedure

A reaction vial was charged with tetrabutylammonium 2-cyanobenzo[d]thiazol-6-olate (209 mg, 1.19 mmol), (E)-2-(3-iodoprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (386 mg, 1.31 mmol) and 15 mL of dry dichloromethane. The vial was sealed, and the solution was heated in an oil bath at 80° C. overnight (˜16 hours). The crude reaction mixture was added to 1 gram of celite, and the solvent was evaporated under vacuum. The product was purified by silica gel chromatography using an increasing gradient of ethyl acetate in dichloromethane as eluent. This gave 166 mg of (E)-6-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)oxy)benzo[d]thiazole-2-carbonitrile as a colorless oil that crystallized to a white solid upon standing at ambient temperature.

Workup

customA reaction
customThe vial was sealed
customThe crude reaction mixture
additionwas added to 1 gram of celite
customthe solvent was evaporated under vacuum
customThe product was purified by silica gel chromatography
customThis gave 166 mg of (E)-6-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)oxy)benzo[d]thiazole-2-carbonitrile as a colorless oil that crystallized to a white solid
customupon standing at ambient temperature

Sources & evidence

ORD record: ord-f3416c70632a4083a849de65f7fd4e7e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785652B2

Reaction notes

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