Sodium Chloride → 3-(Morpholin-4-yl)-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

HRID 1055643ノート

反応式

HRID 1055643 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+].[Cl-].[Na+]>C1(C)C=CC=CC=1.NCCC1C=CC=CC=1[Pd]Cl.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.COC(C)(C)C>[N:17]1([C:2]2[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=2)[C:5]([OH:7])=[O:6])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

参加物

8

反応物 5

HCID 5234Sodium ChlorideHCID 8083MorpholineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 581374213-Bromo-5-(pentafluorosulfur)benzoic acid

生成物 1

HCID 896996563-(Morpholin-4-yl)-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

試薬・触媒・溶媒 2

HCID 178439012HCID 178439012、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

1.5 g (4.6 mmol) of the compound of Example 15A and 0.48 g (5.5 mmol) of morpholine were dissolved in 15 ml of toluene, and the mixture was degassed with argon. 75 mg (0.09 mmol) of [2-(2-aminoethyl)phenyl](chloro)palladium-dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphane/tert-butyl methyl ether adduct, 44 mg (0.09 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphane and 1.06 g (11.0 mmol) of sodium tert-butoxide were added successively to this solution. The reaction was stirred in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 130° C. for 30 min. The reaction was then stirred into 10 ml of saturated aqueous sodium chloride solution and extracted twice with in each case 30 ml of ethyl acetate. The organic phase was washed with pH 4 buffer solution, dried over sodium sulphate and concentrated on a rotary evaporator. The residue was dissolved in 5 ml of tert-butyl methyl ether, and 10 ml of pentane were added. The precipitate formed was filtered off and dried. This gave 1.04 g (68% of theory) of the title compound.

後処理

  1. customthe mixture was degassed with argon
  2. extractionextracted twice with in each case 30 ml of ethyl acetate
  3. washThe organic phase was washed with pH 4 buffer solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated on a rotary evaporator
  6. dissolutionThe residue was dissolved in 5 ml of tert-butyl methyl ether
  7. addition10 ml of pentane were added
  8. customThe precipitate formed
  9. filtrationwas filtered off
  10. customdried

出典と根拠

ORDレコード
ord-4f25ee6e347d414db81215b1bf4f5ac4
出典データセット
uspto-grants-2016_07
特許番号
US09394309B2

反応ノート

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