Sodium Carbonate → HCID 86701170, compound

HRID 572129Notes

Reaction equation

HRID 572129 reaction equation
[C:1]([O-:4])([O-])=O.[Na+].[Na+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9](B(O)O)[CH:8]=1>COCCOC.O.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>[CH3:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:9]2[C:8]=1[N:7]=[C:12]([C:9]1[CH:8]=[N:7][CH:12]=[CH:11][CH:10]=1)[C:11]([CH:1]=[O:4])=[CH:10]2

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acid

Product 1

HCID 86701170HCID 86701170, compoundYield 281.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Prepared according to the procedure described for Intermediate 1, utilising Intermediate 32 (10 g, 48.7 mmol), Na2CO3 (7.74 g, 73 mmol), 3-pyridylboronic acid (5.98 g, 48.7 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.81 g, 2.43 mmol) in DME (150 mL) and water (40 mL). The title compound (11.36 g, 94%) was obtained as a brown solid. δH (CDCl3) 10.20 (s, 1H), 9.02 (dd, J 2.3, 0.8 Hz, 1H), 8.86 (s, 1H), 8.80 (dd, J 4.9, 1.7 Hz, 1H), 8.10 (ddd, J 7.9, 2.3, 1.7 Hz, 1H), 7.90 (d, J 8.3 Hz, 1H), 7.78-7.75 (m, 1H), 7.58 (dd, J 8.1, 7.2 Hz, 1H), 7.53 (ddd, J 7.9, 4.9, 0.8 Hz, 1H), 2.88 (s, 3H). LCMS (ES+) 249 (M+H)+, RT 1.41 minutes.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-d8fc20dd75b74b17bdd5c83f50edfcdf
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

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