Sodium Carbonate → HCID 117666981, compound

HRID 712742Notes

Reaction equation

Br[C:2]1[CH:9]=[N:8][CH:7]=[C:6]([Br:10])[C:3]=1[C:4]#[N:5].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH:20]=[C:21]([C:2]2[CH:9]=[N:8][CH:7]=[C:6]([Br:10])[C:3]=2[C:4]#[N:5])[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

3,5-Dibromo-isonicotinonitrile (500 mg, 1.9 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (710 mg, 2.3 mmol) and 2.0 M Na2CO3 aqueous solution (1.9 mL, 3.8 mmol) are added into the 1,4-dioxane (20 mL). Argon gas is bubbled through the solution for 5 min. Then PdCl2dppf (140 mg, 0.19 mmol) is added and the mixture is heated at 100° C. for 3.5 hrs. The reaction mixture is filtered and the filtrate is concentrated to give the crude product. Purification by flash column chromatography affords 295 mg of 5-bromo-4-cyano-3′,6′-dihydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester.

Workup

customArgon gas is bubbled through the solution for 5 min
filtrationThe reaction mixture is filtered
concentrationthe filtrate is concentrated
customto give the crude product
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-3f4a60f8c3844333a6dac9ca2fcd3fa0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181272B2

Reaction notes

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