Sodium Carbonate → HCID 58084233, compound

HRID 931354Notes

Reaction equation

HRID 931354 reaction equation
Br[C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[N:8]([CH3:11])[N:9]=[CH:10][C:3]=12.[CH3:12]B1OB(C)OB(C)O1.[C:21](=O)([O-])[O-].[Na+].[Na+]>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>[CH3:11][N:8]1[C:4]2[CH2:5][NH:6][CH2:7][C@@H:2]([CH3:12])[C:3]=2[CH:10]=[N:9]1.[CH3:11][N:8]1[C:4]2=[CH:5][N:6]=[CH:7][C:2]([CH3:21])=[C:3]2[CH:10]=[N:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 574072TrimethylboroxineHCID 576069364-Bromo-1-methyl-1H-pyrazolo(3,4-c)pyridine

Product 2

HCID 58084233HCID 58084233, compoundHCID 117678281(4S)-1,4-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The requisite (4S)-1,4-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine was prepared in the following manner. Reaction of C8 at elevated temperature with trimethylboroxin in the presence of sodium carbonate and tetrakis(triphenylphosphine)palladium(0) afforded 1,4-dimethyl-1H-pyrazolo[3,4-c]pyridine. This material was reduced using the method described for synthesis of C9 from C8 in Example 2; the product was subjected to supercritical fluid chromatography to separate the enantiomers (Column: Chiral Technologies, Chiralpak IC, 5 μm; Eluent: 4:1 carbon dioxide/methanol). The second-eluting enantiomer was collected and used for synthesis of Example 20. The absolute stereochemistry was arbitrarily assigned.

Sources & evidence

ORD record
ord-0bc8cd0625124c1e8333d85f505afbbf
Source dataset
uspto-grants-2016_03
Patent number
US09296761B2

Reaction notes

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