Sodium Carbonate → HCID 67051485, compound

HRID 2114051Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[C:12]([C:20]3[CH:24]=[CH:23][O:22][CH:21]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:25]([Si:28]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[N:29]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30]1)([CH3:27])[CH3:26].[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.CCO>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:31]4[CH:32]=[CH:33][N:29]([Si:28]([CH:37]([CH3:39])[CH3:38])([CH:40]([CH3:42])[CH3:41])[CH:25]([CH3:26])[CH3:27])[CH:30]=4)[CH:18]=[C:13]3[C:12]([C:20]3[CH:24]=[CH:23][O:22][CH:21]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 30 (31.6 mg, 0,078 mmol), 1-triisopropylsilanyl-1H-pyrrole-3-boronic acid (31 mg, 0.12 mmol), PdCl2(PPh3)2 (6 mg, 7.8 μmol), LiCl (10 mg, 0.24 mmol), aqueous 1.0 M Na2CO3 (200 μL, 0.2 mmol), EtOH (0.47 mL) and toluene (0.47 mL) were heated at 85° C. over weekend. After cooling the organic layer was separated and purified by PTLC using AcOEt:hexane=3:7 as eluent to give the product 31 as a colourless oil (15.3 mg, 36%). 1H NMR (400 MHz, CDCl3) δ 1.13 (d, J=7.5 Hz, 18H), 1.49 (septet, J=7.5 Hz, 3H), 6.60 (dd, J=2.7, 1.5 Hz, 1H), 6.71 (dd, J=1.8, 0.79 Hz, 1H), 6.84 (t, J=2.5 Hz, 1H), 7.05 (t, J=1.7 Hz, 1H), 7.48 (t, J=8.0 Hz, 2H), 7.56 (m, 2H), 7.78 (s, 1H), 7.83 (s, 1H), 7.99 (d, J=2.0 Hz, 1H), 8.20 (m, 1H), 8.23 (s, 1H), 8.68 (d, J=2.0 Hz, 1H).

Workup

temperatureAfter cooling the organic layer
customwas separated
custompurified by PTLC

Sources & evidence

ORD record: ord-fcc6773088844ca79cf61d5019ea5e41
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432375B2

Reaction notes

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