Sodium Carbonate → HCID 59362525、化合物

HRID 1625445ノート

反応式

HRID 1625445 の反応式
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=[C:13]3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:21][C:22]1[CH:23]=[C:24]([CH:46]=[CH:47][C:48]=1[F:49])[CH2:25][N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([NH:34][CH2:35][C:36]2[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=2)=[O:33])[C:27]1=[O:45].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=[C:13]3[C:12]([C:40]3[CH:41]=[C:36]([CH:37]=[CH:38][CH:39]=3)[CH2:35][NH:34][C:32]([C:28]3[C:27](=[O:45])[N:26]([CH2:25][C:24]4[CH:46]=[CH:47][C:48]([F:49])=[C:22]([F:21])[CH:23]=4)[CH:31]=[CH:30][CH:29]=3)=[O:33])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 242292401-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridineHCID 59362353HCID 59362353、化合物

生成物 1

HCID 59362525HCID 59362525、化合物収率 85%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

Into a vial was dissolved 1-benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (581 mg, 0.00125 mol) and 3-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-phenylboronic acid (453 mg, 0.00114 mol) and palladium acetate (13 mg, 0.000057 mol; Strem) and triphenylphosphine (32 mg, 0.00012 mol; Aldrich) in acetone (5.4 mL, Acros;). To this was added 2.0 M of sodium carbonate in water (1.8 mL). The vial was flushed under an atmosphere of argon and sealed and was heated at 75 Celsius for 1 hour. The reaction was evaporated then diluted with methylene chloride, washed with water, dried with magnesium sulfate, filtered, and concentrated. The residue was taken up in methylene chloride and purified by silica gel chromatography using hexanes/ethyl acetate as eluent (Rf=0.33 in 1:3 hexanes/ethyl acetate) to yield 663.8 mg (85%) of product. MS m/z=689.09 M+H.

後処理

  1. customThe vial was flushed under an atmosphere of argon
  2. customsealed
  3. customThe reaction was evaporated
  4. additionthen diluted with methylene chloride
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-f9206798bf2f4424b2a7930a856aa84b
出典データセット
uspto-grants-2014_07
特許番号
US08778977B2

反応ノート

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