Cesium fluoride → HCID 86694398, compound

HRID 535412Notes

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:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[CH:28]=[N:27][CH:26]=[CH:25]3)[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:34][C:35]1[C:39](B(O)O)=[C:38]([CH3:43])[O:37][N:36]=1.[F-].[Cs+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C(Cl)Cl.O1CCOCC1>[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]([C:39]2[C:35]([CH3:34])=[N:36][O:37][C:38]=2[CH3:43])=[C:15]([C:20]#[C:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[CH:28]=[N:27][CH:26]=[CH:25]3)[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of tert-butyl-N-[1-[[5-bromo-6-(2-isoquinolin-6-ylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate C2b (300 mg, 0.59 mmol), (3,5-dimethyl-1,2-oxazol-4-yl)boronic acid (166 mg, 1.18 mmol), CsF (358 mg, 2.36 mmol) tris-(dibenzylideneacetone)dipalladium(0) (41 mg, 0.06 mmol), tri-tert-butylphosphonium tetrafluoroborate (34 mg, 0.12 mmol) and dioxane (4.5 ml) is stirred under argon atmosphere at 50° C. for 2 h. The mixture is diluted with DCM and extracted with a saturated aqueous solution of NaHCO3. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 191 mg (62%). HPLC-MS: M+H=526; tR=1.89 min (*Method—2).

Workup

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

Sources & evidence

ORD record: ord-56f38fd93b6542f0a1d4636985c8f478
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859541B2

Reaction notes

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