Water → HCID 66591177, compound

HRID 1894808Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=2)O1.Br[C:24]1[N:29]=[C:28]([N:30]([CH3:38])C(=O)OC(C)(C)C)[CH:27]=[CH:26][CH:25]=1.[OH2:39].CN(C)[CH:42]=[O:43]>P([O-])([O-])([O-])=O.[K+].[K+].[K+].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>[C:12]([O:39][C:42]([CH2:38][NH:30][C:28]1[N:29]=[C:24]([C:9]2[CH:10]=[CH:11][C:12]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:14]=2)[CH:25]=[CH:26][CH:27]=1)=[O:43])([CH3:15])([CH3:13])[CH3:11]

Participants

Conditions

Temperature: 90 °C

Procedure

1.25 g (4.13 mmol, 1.2 eq) of ethyl 3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]acrylate and 1.0 g (3.48 mmol, 1 eq) of tert-butyl (6-bromopyrid-2-yl)-methylcarbamate are dissolved in 15 ml of a 6/1 mixture of dimethylformamide and of 2M potassium phosphate solution. 200 mg (0.173 mmol, 5 mol %) of tetrakis(triphenylphosphine)palladium are added. The mixture is stirred for 3 hours at 90° C. The reaction is stopped by adding 30 mL of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate). 850 mg of ethyl 3-{-4-[6-(tert-butoxycarbonylmethylamino)pyrid-2-yl]phenyl}acrylate are obtained. Yield=64%.

Workup

extractionis then extracted with ethyl acetate
dry with materialdried over sodium sulfate
customThe solvents are evaporated off
customthe residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate)

Sources & evidence

ORD record: ord-fbd0890b3e2844ecaa6a7fac0fd03906
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513297B2

Reaction notes

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