Sodium Carbonate → HCID 9931845, compound

HRID 1856708Notes

Reaction equation

[Si]([O:8][C@H:9]([CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C@H:10]([CH3:21])[O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.Br[C:31]1[CH:32]=[C:33]([S:36]([NH2:39])(=[O:38])=[O:37])[S:34][CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.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:8][C@H:9]([CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C@H:10]([CH3:21])[O:11][C:12]1[CH:13]=[CH:14][C:15]([C:31]2[CH:32]=[C:33]([S:36]([NH2:39])(=[O:38])=[O:37])[S:34][CH:35]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Prepared by the method outlined in Example 15g) from (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-yl-butoxy]benzeneboronic acid (0.200 g, example 15f)), 4-bromothiophene-2-sulfonic acid amide (0.145 g, Example 42a)), 2M aqueous sodium carbonate (0.5 ml) and tetrakis(triphenylphosphine)palladium(0) (0.025 g) in ethanol (3 ml). The mixture was heated at 90° C. for 4 hours and after cooling to room temperature the mixture was concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate to afford the title compound as a solid (0.134 g).

Workup

customPrepared by the method
temperatureafter cooling to room temperature the mixture
concentrationwas concentrated under reduced pressure
customThe residue was purified by column chromatography over silica eluting with ethyl acetate

Sources & evidence

ORD record: ord-b86538fabf504f85a7f06e22701445c7
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143751

Reaction notes

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