3-Iodobenzyl alcohol → HCID 67047723, compound

HRID 606951Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C[Si]([C:23]#[C:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([CH:32]=1)[C:30]#[N:31])(C)C.I[C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37][OH:38]>O1CCCC1.C(N(CC)CC)C.[Br-].[Zn+2].[Br-].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>[OH:38][CH2:37][C:36]1[CH:35]=[C:34]([C:23]#[C:24][C:25]2[CH:26]=[N:27][CH:28]=[C:29]([CH:32]=2)[C:30]#[N:31])[CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Add a 1 M solution of tetrabutylammonium fluoride in THF (3.33 mL, 3.33 mmol) to a solution of 5-trimethylsilanylethynyl-nicotinonitrile, (prepared as described in PREPARATION 3), (0.801 g, 4.00 mmol), in tetrahydrofuran (8.3 mL) and triethylamine (3.34 mL). After 5 min add zinc (II) bromide (1.56 g, 5.99 mmol), 3-iodobenzyl alcohol (0.42 mL, 3.33 mmol), and tetrakis(triphenylphosphine)palladium (0) (269 mg, 0.233 mmol). Heat to 55° C. for 2 h, cool to room temperature, and filter through diatomaceous earth. Purify by silica gel chromatography, eluting with 80:20 to 60:40 (1:1 hexanes:dichloromethane):ethyl acetate, to give the title compound as a yellow crystalline solid (380 mg, 49%).

Workup

temperaturecool to room temperature
filtrationfilter through diatomaceous earth
customPurify by silica gel chromatography
washeluting with 80:20 to 60:40 (1:1 hexanes:dichloromethane)

Sources & evidence

ORD record: ord-058f0731d9ab47339e33092feda238af
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915424B2

Reaction notes

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