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Sodium Carbonate → N-(3.4-Dimethyl-5-isoxazolyl)-2'-formyl-4'-(2-pyrimidinyl) [1,1-biphenyl]-2-sulfonamide

HRID 1956965
ノート
印刷プレビュー

反応式

HRID 1956965 の反応式
B([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([C:20]1[O:24][N:23]=[C:22]([CH3:25])[C:21]=1[CH3:26])COCCOC)(=[O:12])=[O:11])(O)O.C(=O)([O-])[O-].[Na+].[Na+].Br[C:34]1[CH:41]=[CH:40][C:39]([C:42]2[N:47]=[CH:46][CH:45]=[CH:44][N:43]=2)=[CH:38][C:35]=1[CH:36]=[O:37]>C1(C)C=CC=CC=1.CCO.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:25][C:22]1[C:21]([CH3:26])=[C:20]([NH:13][S:10]([C:5]2[C:4]([C:34]3[CH:41]=[CH:40][C:39]([C:42]4[N:47]=[CH:46][CH:45]=[CH:44][N:43]=4)=[CH:38][C:35]=3[CH:36]=[O:37])=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:11])=[O:12])[O:24][N:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 107862242-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamideHCID 186631922-Bromo-5-(2-pyrimidinyl)benzaldehyde

生成物 1

HCID 18663185N-(3.4-Dimethyl-5-isoxazolyl)-2'-formyl-4'-(2-pyrimidinyl) [1,1-biphenyl]-2-sulfonamide収率 116.3%

試薬・触媒・溶媒 4

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 702Ethanol溶媒
HCID 962Water溶媒
HCID 1140Toluene溶媒

実験手順

To a solution of 0.554 g (1.188 mmol) of 2-borono-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide (prepared as described in U.S. patent application Ser. No. 08/603,975, filed Feb.20, 1996 by Murugesan et al. (Attorney Docket No. HA662d)) and 0.0578 g (0.05 mmol) of tetrakis(triphenylphosphine)-palladium(0) in 20 mL of toluene under argon, 10 mL of 2M aqueous sodium carbonate was added followed by 0.25 g (0.95 mmol) of the title compound of Step E added in 10 mL of 95% EtOH. The mixture was refluxed for 2 hrs and then diluted with 100 mL of water and extracted with 3×50 mL of EtOAc. The combined organic extracts were washed once with 100 mL of brine and dried and evaporated. The residue was chromatographed on 100 mL of silica gel using Hexanes/EtOAc 1:1 to afford 0.48 g (80%) of the title compound of this step as a colorless gum.

後処理

  1. temperatureThe mixture was refluxed for 2 hrs
  2. extractionextracted with 3×50 mL of EtOAc
  3. washThe combined organic extracts were washed once with 100 mL of brine
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on 100 mL of silica gel

出典と根拠

ORDレコード
ord-0bd75b1ef4ed4203958c6bb7fe1546dc
出典データセット
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05780473

反応ノート

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