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Sodium Bicarbonate → 2-cyano-2-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-acetamide

HRID 886556
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HRID 886556 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[N:11]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH:10]=1.Cl[C:38]1[N:43]=[CH:42][N:41]=[C:40]([CH:44]([C:50]#[N:51])[C:45]([N:47]([CH3:49])[CH3:48])=[O:46])[CH:39]=1.C(=O)(O)[O-].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(#N)C>[C:50]([CH:44]([C:40]1[CH:39]=[C:38]([C:15]2[CH:16]=[C:17]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[CH:10][N:11]([S:27]([C:30]4[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=4)(=[O:28])=[O:29])[C:12]3=[N:13][CH:14]=2)[N:43]=[CH:42][N:41]=1)[C:45]([N:47]([CH3:49])[CH3:48])=[O:46])#[N:51]
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6

반응물 3

HCID 516892Sodium BicarbonateHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 866239462-(6-Chloro-pyrimidin-4-yl)-2-cyano-N,N-dimethyl-acetamide

생성물 1

HCID 598249952-cyano-2-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-acetamide수율 68%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6342Acetonitrile용매

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온도
120 °C

실험 절차

A mixture of 3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.0 g, 2.0 mmole), 2-(6-Chloro-pyrimidin-4-yl)-2-cyano-N,N-dimethyl-acetamide (prepared according to the method published in Tetrahedron Letters (2005) 46, 3587-3589) (670 mg, 3.0 mmole), sodium bicarbonate, (2M aq, 4.9 mmole), acetonitrile (13.2 mL), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (97 mg, 0.12 mmole) was heated in a microwave reactor at 120° C. for 45 min. The crude mixture was concentrated to dryness, suspended in water (50 mL), and stirred for 30 min. The resulting precipitate was filtered off, suspended in ethyl acetate (15 mL), and stirred for 15 h. The precipitate was filtered off, rinsed with ethyl acetate (3×5 mL), and air dried. Recrystallization from ethylacetate/methanol afforded 2-cyano-2-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-acetamide (762 mg, 68% yield) as a bright yellow solid. MS: m/z 567.1 (M+H+).

후처리

  1. customprepared
  2. concentrationThe crude mixture was concentrated to dryness
  3. filtrationThe resulting precipitate was filtered off
  4. stirringstirred for 15 h
  5. filtrationThe precipitate was filtered off
  6. washrinsed with ethyl acetate (3×5 mL), and air
  7. customdried
  8. customRecrystallization from ethylacetate/methanol

출처 및 근거

ORD 기록
ord-2a77cb2b64db4689b2c3e471865c7f28
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242280B2

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