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Sodium Carbonate → 1,4-dimethyl-1H-pyrazolo[3,4-c]pyridine

HRID 931354
ノート
印刷プレビュー

反応式

HRID 931354 の反応式
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
参加物実験手順出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 2

HCID 580842331,4-dimethyl-1H-pyrazolo[3,4-c]pyridineHCID 117678281(4S)-1,4-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine

試薬・触媒・溶媒 1

HCID 178418397
HCID 178418397、化合物
触媒

実験手順

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.

出典と根拠

ORDレコード
ord-0bc8cd0625124c1e8333d85f505afbbf
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09296761B2

反応ノート

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