1,2-Dimethoxyethane → tert-butyl-N-[1-[[4-methyl-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

HRID 535430Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[C:16](Cl)[CH:15]=[C:14]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].OB1OB(O)OB(O)O1.[C:38](=O)([O-])[O-].[K+].[K+].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.O>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[C:16]([CH3:38])[CH:15]=[C:14]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butylN-[1-[[4-chloro-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate D3a (40 mg, 0.10 mmol), 2,4,6-trihydroxy-1,3,5,2,4,6-trioxatriborinane (36 μl, 0.26 mmol), Tetrakis(triphenylphosphine)palladium(0) (16.6 mg, 0.01 mmol), potassium carbonate (41.5 mg, 0.30 mmol), 1,2-dimethoxyethane (600 μl) and water (100 μl) is stirred for 2 day at 80° C. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 2 mg (5%). HPLC-MS: M+H=380; tR=2.18 min (*Method—2).

Workup

concentrationThe mixture is concentrated in vacuo
customthe product purified by RP HPLC

Sources & evidence

ORD record: ord-47b0565d6d17490ba5d267a3005de743
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859541B2

Reaction notes

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