Sodium Hydroxide → HCID 57610352, compound

HRID 516497Notes

Reaction equation

[OH-].[Na+].Br[C:4]1[CH:5]=[C:6]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=[C:12]([C:21]3[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1.[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1B(O)O>COCCOC.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>[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[C:4]1[CH:5]=[C:6]([C:10]2[N:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:13]=[C:12]([C:21]3[CH:22]=[CH:23][C:24]([C:30]4[CH:29]=[CH:28][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH:31]=4)=[CH:25][CH:26]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Sodium hydroxide solution (0.2 g NaOH dissolved in 5 ml of water) and 0.12 g (0.1 mmol) of Pd(PPh3)4 are added to 0.9 g (1.97 mmol) of the triazole obtained in step A) and 0.82 g (4.7 mmol) of naphthalene-2-boronic acid in 15 ml of 1,2-dimethoxy ethane under a nitrogen atmosphere. The reaction mixture is heated at 85° C. for 24 h, cooled and extracted with ethyl acetate. The organic solvent is removed and the residue is chromatographed. 0.4 g of desired compound A-21 is obtained as greenish solid (yield (40%); mp: 156-158° C.).

Workup

temperaturecooled
extractionextracted with ethyl acetate
customThe organic solvent is removed
customthe residue is chromatographed

Sources & evidence

ORD record: ord-03d2633a4f0449dfa9b854b41c6bede6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09113536B2

Reaction notes

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