Triethylamine → 2-[5-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzofuran-2-yl]-ethanol

HRID 2251124Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

4-(6,7-Dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-2-iodo-phenol (440 mg, 1.17 mmol), homopropargyl alcohol (147.3 mg, 2.1 mmol) and triethyl amine (295 mg, 2.92 mmol) were dissolved in DMF (15 ml). To this solution was added copper (I) iodide (66.3 mg, 0.34 mmol) and bis-triphenylphosphine palladium (II) chloride (81.9 mg, 0.117 mmol). The reaction was flushed with nitrogen and heated at 65° C. for 12 hours. Solvent was removed under reduced pressure and the residue purified on silica gel (10%-75% EtOAc in hexane) to give 2-[5-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzofuran-2-yl]-ethanol.

Workup

customThe reaction was flushed with nitrogen
customSolvent was removed under reduced pressure
customthe residue purified on silica gel (10%-75% EtOAc in hexane)

Sources & evidence

ORD record: ord-b673d157d7874a73989d9a3c5a7f91ba
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319103B2

Reaction notes

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