Sodium Carbonate → HCID 86694401, compound

HRID 535414Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[N:7]([CH:9]([CH3:32])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([C:20]#[C:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[N:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[C:36](B(O)O)[CH:35]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>C(Cl)Cl.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.O.CO>[C:1]([O:5][C:6](=[O:33])[N:7]([CH3:8])[CH:9]([CH3:32])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:36]2[CH:35]=[N:34][C:43]3[C:38]([CH:37]=2)=[CH:39][CH:40]=[CH:41][CH:42]=3)=[C:15]([C:20]#[C:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)[N:14]=1)=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of tert-butyl-N-[1-[[5-bromo-6-(2-naphthalen-2-ylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate C2c (150 mg, 0.30 mmol), quinolin-3-ylboronic acid (61 mg, 0.35 mmol), Dichlorobis(triphenylphosphine)palladium(II) (40 mg, 0.06 mmol), Na2CO3 (63 mg, 0.59 mmol), dioxane (1 ml), MeOH (0.2 ml) and water (0.1 ml) is stirred under argon atmosphere for 2 h at 85° C. The mixture is diluted with DCM and extracted with a saturated aqueous solution of NaHCO3. The combined organic layers are dried over MgSO4, concentrated in vacuo and the product purified by RP HPLC. Yield: 91 mg (55%).

Workup

extractionextracted with a saturated aqueous solution of NaHCO3
dry with materialThe combined organic layers are dried over MgSO4
concentrationconcentrated in vacuo
customthe product purified by RP HPLC

Sources & evidence

ORD record: ord-1351bc3bbae344c9bcb393bfac87f6f5
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859541B2

Reaction notes

Loading…