Triethylamine → 2-Benzyloxy-6-{(E)-4-[6-benzyloxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-but-3-enyloxy}-N,N-dimethylbenzamide

HRID 643883Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([N:20]2[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]2)=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14](Br)[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([O:35][C:36]1[CH:46]=[CH:45][CH:44]=[C:43]([O:47][CH2:48][CH2:49][CH:50]=[CH2:51])[C:37]=1[C:38]([N:40]([CH3:42])[CH3:41])=[O:39])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(N(CC)CC)C>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:28]([O:35][C:36]1[CH:46]=[CH:45][CH:44]=[C:43]([O:47][CH2:48][CH2:49]/[CH:50]=[CH:51]/[C:14]2[CH:15]=[CH:16][C:17]3[C:12](=[CH:11][C:10]([N:20]4[CH2:21][C:22](=[O:27])[NH:23][S:24]4(=[O:26])=[O:25])=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:18]=3)[CH:13]=2)[C:37]=1[C:38]([N:40]([CH3:42])[CH3:41])=[O:39])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a microwave vial is added 5-(3-benzyloxy-7-bromonaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (36 mg, 0.082 mmol), 2-benzyloxy-6-but-3-enyloxy-N,N-dimethylbenzamide (53 mg, 0.163 mmol), Pd(OAc)2 (5 mg, 0.021 mmol) and 2-(di-t-butylphosphino)biphenyl (6 mg, 0.021 mmol). The mixture is diluted with acetonitrile (2 mL) and triethylamine (0.023 mL, 0.163 mmol). This is stirred in a microwave for 30 min at 100° C. The reaction mixture is filtered, acidified with 1 N HCl solution and extracted with EtOAc. The organic layer is concentrated and used directly in the next step.

Workup

filtrationThe reaction mixture is filtered
extractionextracted with EtOAc
concentrationThe organic layer is concentrated

Sources & evidence

ORD record: ord-7f4dc55d4d6745dab7be9952ca919edc
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700633B2

Reaction notes

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