Triethylamine → 5-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 660492Notes

Reaction equation

[CH2:1]([O:8][CH2:9][N:10]1[C:14]([CH:15]=[CH2:16])=[CH:13][CH:12]=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:24][C:25]1[CH:30]=[C:29](I)[CH:28]=[CH:27][C:26]=1[N:32]1[S:36](=[O:38])(=[O:37])[N:35]([CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:34](=[O:45])[CH2:33]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:17]([O:24][C:25]1[CH:30]=[C:29](/[CH:16]=[CH:15]/[C:14]2[N:10]([CH2:9][O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:11]=[CH:12][CH:13]=2)[CH:28]=[CH:27][C:26]=1[N:32]1[S:36](=[O:37])(=[O:38])[N:35]([CH2:39][CH2:40][Si:41]([CH3:43])([CH3:42])[CH3:44])[C:34](=[O:45])[CH2:33]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-benzyloxymethyl-5-vinyl-1H-pyrazole (385 mg, 1.80 mmol), 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (500 mg, 0.90 mmol), Pd(OAc)2 (13 mg, 0.06 mmol), P(o-tolyl)3 (43 mg, 0.14 mmol) and triethylamine (0.21 mL, 1.5 mmol) in MeCN is heated at 110° C. for 30 min in a microwave apparatus. The reaction mixture is concentrated and chromatographed using a gradient of 15-30% EtOAc/hexanes to afford the title compound as a yellow oil: (M+1)+=631.

Workup

concentrationThe reaction mixture is concentrated
customchromatographed

Sources & evidence

ORD record: ord-e2b9bbed4e7c4662ada36417718d7576
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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