Sodium Carbonate → Ammonia

HRID 450949노트

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HRID 450949 반응식
Br[C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([CH3:32])([CH3:31])[CH2:14][CH2:15][C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]#[N:18])[CH2:9][CH2:8]1.[OH:36][C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][CH:42]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.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]>[NH3:10].[OH:36][C:37]1[CH:42]=[C:41]([C:2]2[CH:35]=[CH:34][CH:33]=[C:4]([CH2:5][O:6][CH:7]3[CH2:12][CH2:11][N:10]([C:13]([CH3:31])([CH3:32])[CH2:14][CH2:15][C:16]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:17]#[N:18])[CH2:9][CH2:8]3)[CH:3]=2)[CH:40]=[CH:39][CH:38]=1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 59423969HCID 59423969, 화합물

생성물 2

HCID 222AmmoniaHCID 59423956HCID 59423956, 화합물

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

1,1′-Bis (diphenylphosphino)ferrocenedichloro palladium(II) (8 mg, 0.09 mmol) was added to a suspension of the product of example 87 (100 mg, 0.19 mmol), 3-hydroxyphenylboronic acid (52 mg, 0.038 mmol) and sodium carbonate (40 mg, 0.038 mmol) in tetrahydrofuran (5 mL) and water (1 mL) and the mixture was heated at 60° C. for 12 hours. The suspension was allowed to cool to room temperature and then evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 99:1:0 to 98:2:0.2, to give the title compound as a gum in 72% yield.

후처리

  1. temperatureto cool to room temperature
  2. customevaporated to dryness under reduced pressure
  3. customThe residue was purified by chromatography on silica gel
  4. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-f314cd21b92c4fbabacb99f2c3481d67
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486992B2

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