5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehyde → HCID 86627823, compound

HRID 1982947Notes

Reaction equation

HRID 1982947 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:14]4[CH:24]=[CH:25][C:26]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:27][C:13]=4[N:12]=3)=[N:9][N:8]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:5]2=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:49]2[CH:50]=[C:51]([CH:55]=[O:56])[CH:52]=[N:53][CH:54]=2)O1>C([O-])([O-])=O.[Na+].[Na+].COCCOC.C(Cl)Cl.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>[F:30][C:29]([F:31])([F:32])[O:28][C:26]1[CH:25]=[CH:24][C:14]2[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])[C:11]([C:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([C:49]5[CH:50]=[C:51]([CH:55]=[O:56])[CH:52]=[N:53][CH:54]=5)[CH:3]=4)[N:8]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[N:9]=3)=[N:12][C:13]=2[CH:27]=1

Participants

8

Reactant 2

HCID 49926405-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehydeHCID 68886473HCID 68886473, compound

Product 1

HCID 86627823HCID 86627823, compound

Reagents, catalysts & solvents 5

HCID 10340Sodium CarbonateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-3-[5-trifluoromethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine Compound 16e (0.12 g, 0.18 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-3-carbaldehyde Compound 15b (0.063 g, 0.27 mmol) and 2M Na2CO3 (5 drops) were mixed in DME (10 mL) in a reaction tube. The resulting yellowish clear solution was degassed with nitrogen for 15 minutes, then tetrakis(triphenylphosphine)palladium(0) (0.021 g, 0.018 mmol) was added and the reaction tube was sealed and heated at 100° C. overnight. The sealed tube was cooled and opened and the contents was diluted with DCM and H2O, then filtered through Celite. The solvent was evaporated to dryness to provide 5-[3-[5-trifluoromethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-pyridine-3-carbaldehyde Compound 17a (0.241 g) as a brown semi-solid which was used directly in the next step without further purification. LCMS single peak, 4.614 min, MS (ESI) m/z 685.2 (M+H+).

Workup

  1. customThe resulting yellowish clear solution was degassed with nitrogen for 15 minutes
  2. customthe reaction tube was sealed
  3. temperatureThe sealed tube was cooled
  4. filtrationfiltered through Celite
  5. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-2064d39b3af9436389730e64a0895542
Source dataset
uspto-grants-2009_06
Patent number
US07541367B2

Reaction notes

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