Sodium Carbonate → HCID 67497574, 화합물

HRID 1628302노트

반응식

HRID 1628302 반응식
Cl.Br[C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]2[CH2:7][CH2:8][NH:9][C:10]=2[CH:11]=1.[N:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=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.CN(C=O)C>[N:16]1[CH:21]=[CH:20][C:19]([C:3]2[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]3[CH2:7][CH2:8][NH:9][C:10]=3[CH:11]=2)=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 72207945HCID 72207945, 화합물

생성물 1

HCID 67497574HCID 67497574, 화합물수율 100.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매2회HCID 6228Dimethylformamide용매

실험 절차

To a 100 ml flask was added methyl 6-bromoindoline-4-carboxylate 54.1.B (2000 mg, 7.8 mmole), 4-pyridylboronic acid (1152 mg, 9.4 mmole, available from Maybridge), tetrakis(triphenylphosphine)palladium (1805 mg, 1.6 mmole, available from Strem), 30 ml of DMF and 10 ml of saturated sodiumcarbonate. The reaction was stirred at 70° C. for 18 hours at which time additional tetrakis(triphenylphosphine)palladium (900 mg, 0.8 mmole) was added. After an additional 12 hours, the reaction mixture was partitioned between 1000 ml EtAc and 300 ml of water. The organic solvent was removed by rotary evaporation to give methyl 6-(pyridin-4-yl)indoline-4-carboxylate 54.1.C (1986 mg, 100% yield) which was used with no further purification.

후처리

  1. additionwas added
  2. customthe reaction mixture was partitioned between 1000 ml EtAc and 300 ml of water
  3. customThe organic solvent was removed by rotary evaporation

출처 및 근거

ORD 기록
ord-0ab59c2038594397a0e5c2374efd2527
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785468B2

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