Sodium Carbonate → HCID 67497574、化合物

HRID 1628302ノート

反応式

HRID 1628302 の反応式
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

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 72207945HCID 72207945、化合物

生成物 1

HCID 67497574HCID 67497574、化合物収率 100.1%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒2 回HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0ab59c2038594397a0e5c2374efd2527
出典データセット
uspto-grants-2014_07
特許番号
US08785468B2

反応ノート

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