Potassium Carbonate → HCID 89499550、化合物

HRID 333672ノート

反応式

HRID 333672 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH3:15])=[N:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[CH3:24][Si:25]([C:28]#[C:29][B-](F)(F)F)([CH3:27])[CH3:26].[K+].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C>[CH3:15][O:14][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[C:2]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])=[C:3]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:4]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 23673582PotassiuM (2-triMethylsilyl)ethynyltrifluoroborateHCID 53379588HCID 53379588、化合物2 回

生成物 1

HCID 89499550HCID 89499550、化合物収率 93%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of the compound 4-bromo-1,7-dimethoxy-3-(4-methoxyphenyl)isoquinoline (compound 26) (187 mg, 0.5 mmol), potassium (trimethylsilyl)ethynyltrifluoroborate (133 mg, 0.65 mmol), palladium diacetate (3.5 mg, 0.015 mmol), RuPhos (14 mg, 0.03 mmol) and potassium carbonate (318 mg, 1.5 mmol) dissolved in 2 mL of a distilled THF/degassed H2O mixture (10/1) is refluxed under argon for 2 hours. The reaction medium is filtered on silica then condensed under vacuum. The crude is purified on a silica column (cyclohexane/dichloromethane, 7/3). 182 mg (93%) of the 1,7-dimethoxy-3-(4-methoxyphenyl)-4-((trimethylsilyl)ethynyl)isoquinoline intermediate is obtained in the form of a brown solid which is used directly in the following stage,

後処理

  1. customdegassed H2O mixture (10/1)
  2. temperatureis refluxed under argon for 2 hours
  3. filtrationThe reaction medium is filtered on silica
  4. customcondensed under vacuum
  5. customThe crude is purified on a silica column (cyclohexane/dichloromethane, 7/3)

出典と根拠

ORDレコード
ord-564cf0f97e8542a087471acfd4caaa68
出典データセット
uspto-grants-2014_11
特許番号
US08883763B2

反応ノート

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