Hydrochloric Acid → HCID 76284978、化合物

HRID 1778769ノート

反応式

HRID 1778769 の反応式
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[N:21](C3CCCCO3)[N:20]=[C:19](I)[C:16]2=[N:17][CH:18]=1.[CH3:29][N:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[N:31]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.C(Cl)(=O)C>O1CCOCC1.O.CO.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>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[NH:21][N:20]=[C:19]([C:33]3[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=3)[C:16]2=[N:17][CH:18]=1

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 10796Cesium carbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86722865HCID 86722865、化合物

生成物 1

HCID 76284978HCID 76284978、化合物収率 20.5%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

A mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-b]pyridine (25 mg, 0.047 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (12 mg, 0.056 mmol), tetrakis(triphenylphosphine)palladium(0) (3 mg, 0.002 mmol), and cesium carbonate (46 mg, 0.14 mmol) in 1,4-dioxane (0.5 mL) and water (0.07 mL) in a reaction vial was degassed, sealed, and stirred at 85° C. for 3 h. After cooling the mixture was concentrated and the residue was dissolved in methanol (0.4 mL, 10 mmol). To the solution was added HCl solution previously prepared from acetyl chloride (0.3 mL) in methanol (0.3 mL). The mixture was stirred at r.t. for 1 h then concentrated, diluted with methanol, and purified by RP-HPLC (pH=2) to afford the desired product (3.9 mg) as a TFA salt. LCMS (M+H)+=404.1.

後処理

  1. customin a reaction
  2. customvial was degassed
  3. customsealed
  4. temperatureAfter cooling the mixture
  5. concentrationwas concentrated
  6. stirringThe mixture was stirred at r.t. for 1 h
  7. concentrationthen concentrated
  8. additiondiluted with methanol
  9. custompurified by RP-HPLC (pH=2)

出典と根拠

ORDレコード
ord-352e8a6c4178457794ddb81fc7d4ddf8
出典データセット
uspto-grants-2016_02
特許番号
US09266892B2

反応ノート

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