Potassium Hydroxide → HCID 58167971, compound

HRID 1029125Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[Cl:17][C:18]1[CH:19]=[C:20]([NH2:31])[CH:21]=[CH:22][C:23]=1[S:24][C:25]1[N:26]([CH3:30])[CH:27]=[CH:28][N:29]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[OH-].[K+]>C(O)(CC)(C)C.CO.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:17][C:18]1[CH:19]=[C:20]([NH:31][C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)[CH:21]=[CH:22][C:23]=1[S:24][C:25]1[N:26]([CH3:30])[CH:27]=[CH:28][N:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Compound 83 (100 mg, 0.43 mmol), 3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamine (156 mg, 0.65 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (21 mg, 0.04 mmol), and KOH (97 mg, 1.73 mmol) were suspended in tert-amyl alcohol (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered, and purified via prep-LC-MS to provide 156 (4 mg, 2% yield) as a solid. LC-MS (M+H=434, obsd.=434).

Workup

filtrationfiltered
custompurified via prep-LC-MS

Sources & evidence

ORD record: ord-d7665df0868446e4b325cdb7e09e8f68
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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