Dichloromethane → 6-(2-Chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-4-fluoro-2-methylbenzo[d]oxazole

HRID 1487680Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([O:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[C:5]2[C:10](B(O)O)=[CH:9][N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[N:7]=1.Br[C:29]1[CH:38]=[C:37]([F:39])[C:32]2[N:33]=[C:34]([CH3:36])[O:35][C:31]=2[CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>O1CCOCC1.O.Cl[Pd]Cl>[Cl:1][C:2]1[N:3]=[C:4]([O:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[C:5]2[C:10]([C:29]3[CH:38]=[C:37]([F:39])[C:32]4[N:33]=[C:34]([CH3:36])[O:35][C:31]=4[CH:30]=3)=[CH:9][N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(2-Chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)boronic acid (1 equiv), 6-bromo-4-fluoro-2-methylbenzo[d]oxazole (1.1 equiv), sodium carbonate (3 equiv) and [1,1′-Bisdiphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (0.1 equiv) were suspended in 1,4-dioxane/water, flushed with nitrogen, and stirred at 90° C. for 2 h. The reaction mixture was purified by silica gel chromatography (0 to 60% ethyl acetate in hexane) to give the title compound (72% yield). MS (ESI) m/z 517.3 [M+H]+.

Workup

customflushed with nitrogen
customThe reaction mixture was purified by silica gel chromatography (0 to 60% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-e039f26a46de42308678f566a6aed4e8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428509B2

Reaction notes

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