Potassium Phosphate, Tribasic → HCID 86632055, compound

HRID 504461Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:33][CH2:34][C:35]2([CH3:39])[CH2:38][O:37][CH2:36]2)=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:9]32[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[NH:24][C:23]3=[O:32])[CH:7]=1.COB([C:45]#[C:46][Si:47]([CH3:50])([CH3:49])[CH3:48])OC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.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>[Cl:31][C:27]1[CH:26]=[C:25]2[NH:24][C:23](=[O:32])[C:9]3([CH:8]([C:6]4[CH:7]=[C:2]([C:45]#[C:46][Si:47]([CH3:48])([CH3:49])[CH3:50])[CH:3]=[CH:4][C:5]=4[O:33][CH2:34][C:35]4([CH3:39])[CH2:38][O:37][CH2:36]4)[CH2:13][C:12](=[O:14])[NH:11][CH:10]3[C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=3[CH3:22])[C:30]2=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of racemic (2′S,3S,4′R)-4′-[5-bromo-2-(3-methyl-oxetan-3-ylmethoxy)-phenyl]-6-chloro-2′-(5-chloro-2-methyl-phenyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (50 mg, 0.08 mmol), trimethylsilylacetylene boronic acid dimethyl ester (0.7 M, 0.7 mL, 0.49 mmol) and K3PO4 (100 mg, 0.48 mmol) in THF was added Pd(PPh3)4 (15 mg) under argon. The reaction mixture was heated at 80° C. for 20 h, purified by prep-HPLC to give the title compound as a white solid.

Workup

custompurified by prep-HPLC

Sources & evidence

ORD record: ord-3608a66fdd4a43ff96f98fd00ae3f2a3
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776875B2

Reaction notes

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