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Water → HCID 178487698, 화합물

HRID 925971
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HRID 925971 반응식
Br[C:2]1[N:3]=[C:4]([C:7]2[CH:16]=[C:15]([OH:17])[C:14]3[C:9](=[C:10]([Cl:20])[C:11]([O:18][CH3:19])=[CH:12][CH:13]=3)[N:8]=2)[S:5][CH:6]=1.O.C[C:23]([N:25](C)C)=O>[Zn].[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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.[Fe+2]>[Cl:20][C:10]1[C:11]([O:18][CH3:19])=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([C:4]1[S:5][CH:6]=[C:2]([C:23]#[N:25])[N:3]=1)[CH:16]=[C:15]2[OH:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 962WaterHCID 31374DimethylacetamideHCID 178487688HCID 178487688, 화합물

생성물 1

HCID 178487698HCID 178487698, 화합물수율 81%

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매

실험 절차

The compound 262 (286 mg, 1 eq.) in degazed dimethylacetamide (10 mL), and Zn (4.5 mg, 0.09 eq.), Zn(CN)2 (84 mg, 0.6 eq.), Pd2dba3 (21 mg, 0.03 eq.), and dppf (26 mg, 0.06 eq.) were heated at 110° C. under microwaves for 30 min. Then, water was added, the precipitate filtered and dissolved in ethyl acetate, dried, and concentrated under vacuum. The residue was purified by chromatography on a silica gel to give compound 263 as a yellow solid in 81% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 4.07 (s, 3H), 6.79 (br s, 1H), 7.08 (d, J=9.11 Hz, 1H), 8.19 (s, 1H), 8.28 (d, J=9.11 Hz, 1H), 9.74 (br s, 1H); MS (ESI, EI+): m/z=318.15 (MH+).

후처리

  1. filtrationthe precipitate filtered
  2. dissolutiondissolved in ethyl acetate
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography on a silica gel

출처 및 근거

ORD 기록
ord-d6266af399e94643920e9aa3254da276
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284307B2

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