2-Methyl-3-butyn-2-ol → HCID 69322534, compound

HRID 448090Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of product from Example 13 (33 mg, 0.08 mmol), 2-methylbut-3-yn-2-ol (10 mg, 0.1 mmol), CuI (2 mg, 0.01 mmol and Pd(Ph3P)4 (30 mg, 0.03 mmol) in triethylamine (10 mL) was heated at 100° C. for 1 hour. The mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was purified by chromatography (hexane-EtOAc 1:1) to afford 20 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.95 (t, J=7 Hz, 3H), 1.40 (sextet, J=7 Hz, 2H), 1.67 (quintet, J=7 Hz, 2H), 2.34 (s, 3H), 3.85 (s, 3H), 3.95 (t, J=7 Hz, 2H), 5.50 (s, 1H), 6.72 (s, 1H), 7.13 (d, J=9 Hz, 1H), 7.43 (dd, J=9 Hz, 3 Hz, 1H), 7.66 (d, J=3 Hz, 1H); MS (ESI) m/z 420 (M+H)+. Anal calcd for C22H26ClNO3S: C, 62.92; H, 6.24; N, 3.34. Found: C, 62.85; H, 6.28; N, 2.92.

Workup

temperatureThe mixture was then cooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography (hexane-EtOAc 1:1)

Sources & evidence

ORD record: ord-21bcc378935541e59194752f9cec9917
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481574B2

Reaction notes

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