Sodium Carbonate → HCID 59362525, 화합물

HRID 1625445노트

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HRID 1625445 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 59362525HCID 59362525, 화합물수율 85%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f9206798bf2f4424b2a7930a856aa84b
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778977B2

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