Potassium Carbonate → HCID 89499550, 화합물

HRID 333672노트

반응식

HRID 333672 반응식
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

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 23673582PotassiuM (2-triMethylsilyl)ethynyltrifluoroborateHCID 53379588HCID 53379588, 화합물2회

생성물 1

HCID 89499550HCID 89499550, 화합물수율 93%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl촉매HCID 8028Tetrahydrofuran용매

실험 절차

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,

후처리

  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)

출처 및 근거

ORD 기록
ord-564cf0f97e8542a087471acfd4caaa68
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883763B2

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